更新支票列印

Adds a Payee1099 recipient master (encrypted TIN, W-9, optional Member
link), Form1099Box catalog + category->box mapping, a cash-basis year-end
1099 report (per-recipient x box, $600 + missing-W9 flags), recipient
Copy B 1099-NEC PDF + filing CSV, W-9 upload, write-gated TIN reveal, and
a ChurchProfile payer EIN. New Form1099 permission module + admin pages.

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>

API/ROLAC.API.Tests/ROLAC.API.Tests.csproj

@@ -22,6 +22,7 @@
     <PackageReference Include="Moq" Version="4.20.72" />
     <PackageReference Include="Microsoft.EntityFrameworkCore.InMemory" Version="8.0.11" />
     <PackageReference Include="Microsoft.Extensions.Configuration" Version="8.0.0" />
+    <PackageReference Include="Microsoft.AspNetCore.DataProtection" Version="8.0.11" />
   </ItemGroup>
 
   <ItemGroup>

API/ROLAC.API.Tests/Services/ChurchAiConfigProviderTests.cs

@@ -0,0 +1,27 @@
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.Services.Ai;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class ChurchAiConfigProviderTests
+{
+    private static AppDbContext NewDb() =>
+        new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString()).Options);
+
+    [Fact]
+    public async Task GetAsync_returns_defaults_when_no_profile_row()
+    {
+        using var db = NewDb();   // empty DB, no ChurchProfile
+
+        var cfg = await new ChurchAiConfigProvider(db).GetAsync();
+
+        Assert.Equal("Claude", cfg.Provider);
+        Assert.Equal("claude-haiku-4-5-20251001", cfg.ClaudeModel);
+        Assert.Equal("gemini-2.5-flash-lite", cfg.GeminiModel);
+        Assert.Null(cfg.ClaudeApiKey);
+        Assert.Null(cfg.GeminiApiKey);
+    }
+}

API/ROLAC.API.Tests/Services/ChurchProfileServiceTests.cs

@@ -0,0 +1,103 @@
+using System.Security.Claims;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Diagnostics;
+using Moq;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.DTOs.Disbursement;
+using ROLAC.API.Entities;
+using ROLAC.API.Services;
+using ROLAC.API.Services.Logging;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class ChurchProfileServiceTests
+{
+    // ChurchProfile is auditable, so the InMemory store rejects saves unless the
+    // required CreatedBy/UpdatedBy fields are populated. Wire the same audit
+    // interceptor the app uses so seeded entities save cleanly.
+    private static AppDbContext NewDb()
+    {
+        var httpContext = new DefaultHttpContext
+        {
+            User = new ClaimsPrincipal(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, "test-user") })),
+        };
+        var httpContextAccessor = new Mock<IHttpContextAccessor>();
+        httpContextAccessor.Setup(accessor => accessor.HttpContext).Returns(httpContext);
+        return new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .ConfigureWarnings(warnings => warnings.Ignore(InMemoryEventId.TransactionIgnoredWarning))
+            .AddInterceptors(new AuditSaveChangesInterceptor(new CurrentUserAccessor(httpContextAccessor.Object)))
+            .Options);
+    }
+
+    private static UpdateChurchProfileRequest Req(
+        string provider = "Claude", string? claudeKey = null, string? geminiKey = null,
+        string? claudeModel = "m", string? geminiModel = "m") =>
+        new()
+        {
+            Name = "C", NextCheckNumber = 1001, AiProvider = provider,
+            ClaudeModel = claudeModel, GeminiModel = geminiModel,
+            ClaudeApiKey = claudeKey, GeminiApiKey = geminiKey,
+        };
+
+    [Fact]
+    public async Task GetAsync_masks_stored_api_keys()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile
+        {
+            Name = "C", ClaudeApiKey = "sk-ant-abcd1234", GeminiApiKey = "AIzaXYZ9876",
+        });
+        await db.SaveChangesAsync();
+
+        var dto = await new ChurchProfileService(db).GetAsync();
+
+        Assert.Equal("••••••1234", dto.ClaudeApiKeyMasked);
+        Assert.Equal("••••••9876", dto.GeminiApiKeyMasked);
+    }
+
+    [Fact]
+    public async Task UpdateAsync_blank_key_keeps_existing()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", ClaudeApiKey = "sk-keep-0001" });
+        await db.SaveChangesAsync();
+
+        await new ChurchProfileService(db).UpdateAsync(Req(claudeKey: null));
+
+        var p = await db.ChurchProfiles.FirstAsync();
+        Assert.Equal("sk-keep-0001", p.ClaudeApiKey);
+    }
+
+    [Fact]
+    public async Task UpdateAsync_nonblank_key_replaces()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", ClaudeApiKey = "sk-keep-0001" });
+        await db.SaveChangesAsync();
+
+        await new ChurchProfileService(db).UpdateAsync(Req(claudeKey: "sk-new-9999"));
+
+        var p = await db.ChurchProfiles.FirstAsync();
+        Assert.Equal("sk-new-9999", p.ClaudeApiKey);
+    }
+
+    [Fact]
+    public async Task UpdateAsync_sets_provider_and_models()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C" });
+        await db.SaveChangesAsync();
+
+        await new ChurchProfileService(db).UpdateAsync(
+            Req(provider: "Gemini", claudeModel: "claude-x", geminiModel: "gemini-y"));
+
+        var p = await db.ChurchProfiles.FirstAsync();
+        Assert.Equal("Gemini", p.AiProvider);
+        Assert.Equal("claude-x", p.ClaudeModel);
+        Assert.Equal("gemini-y", p.GeminiModel);
+    }
+}

API/ROLAC.API.Tests/Services/DbSeederForm990Tests.cs

@@ -56,6 +56,13 @@ public class DbSeederForm990Tests
         var worship = await db.Ministries.FirstAsync(m => m.Name_en == "Worship");
         Assert.Equal("ManagementGeneral", admin.DefaultFunctionalClass);
         Assert.Equal("Program", worship.DefaultFunctionalClass);
+
+        // Activity/shepherding ministries are an attribution axis only; they default to Program
+        // so adding them never distorts the 990 functional columns.
+        var cellGroups = await db.Ministries.FirstAsync(m => m.Name_en == "Cell Groups");
+        var specialEvents = await db.Ministries.FirstAsync(m => m.Name_en == "Special Events");
+        Assert.Equal("Program", cellGroups.DefaultFunctionalClass);
+        Assert.Equal("Program", specialEvents.DefaultFunctionalClass);
     }
 
     [Fact]
@@ -77,4 +84,59 @@ public class DbSeederForm990Tests
             .FirstAsync(s => s.Name_en == "Accounting & Audit");
         Assert.Equal("11c", audit.Form990Line!.LineCode);
     }
+
+    [Fact]
+    public async Task SeedForm990Lines_MapsAuditCorrectedSubcategories_OffTheLine24CatchAll()
+    {
+        using var db = BuildDb();
+        await DbSeeder.SeedExpenseCategoriesAsync(db);
+        await DbSeeder.SeedForm990ExpenseLinesAsync(db);
+
+        async Task<string> CodeOf(string subEn) =>
+            (await db.ExpenseSubCategories.Include(s => s.Form990Line)
+                .FirstAsync(s => s.Name_en == subEn)).Form990Line!.LineCode;
+
+        // Newly mapped subcategories that previously fell through to line 24.
+        Assert.Equal("13", await CodeOf("Bank & Processing Fees"));
+        Assert.Equal("13", await CodeOf("Rental"));
+        Assert.Equal("13", await CodeOf("Maintenance & Repair"));
+        Assert.Equal("13", await CodeOf("Cleaning Supplies"));
+        Assert.Equal("13", await CodeOf("Craft Supplies"));
+        // Building repairs & maintenance are part of Occupancy (line 16), not equipment (line 13).
+        Assert.Equal("16", await CodeOf("Repairs & Maintenance"));
+        // Appreciation/outreach gifts are deliberately mapped to Other (line 24), not left unmapped.
+        Assert.Equal("24", await CodeOf("Gifts"));
+        // Visitation is a travel/program cost, not a grant to an individual.
+        Assert.Equal("17", await CodeOf("Visit Expenses"));
+        // Missions support paid to individual missionaries → line 2, not line 1 (organizations).
+        Assert.Equal("2",  await CodeOf("Missionary Support"));
+    }
+
+    [Fact]
+    public async Task SeedForm990Lines_RemapsExistingBadMapping_ButNotAdminOverride()
+    {
+        using var db = BuildDb();
+        await DbSeeder.SeedExpenseCategoriesAsync(db);
+        await DbSeeder.SeedForm990ExpenseLinesAsync(db);
+
+        // Simulate a database seeded by the OLD code: Visit Expenses on line 2, Missionary
+        // Support on line 1. Also simulate an admin who deliberately moved one elsewhere.
+        var lineByCode = await db.Form990ExpenseLines.ToDictionaryAsync(l => l.LineCode, l => l.Id);
+        var visit = await db.ExpenseSubCategories.FirstAsync(s => s.Name_en == "Visit Expenses");
+        var missionary = await db.ExpenseSubCategories.FirstAsync(s => s.Name_en == "Missionary Support");
+        var transfer = await db.ExpenseSubCategories.FirstAsync(s => s.Name_en == "Offering Transfer");
+        visit.Form990LineId      = lineByCode["2"];   // old (wrong) value → should be corrected
+        missionary.Form990LineId = lineByCode["1"];   // old (wrong) value → should be corrected
+        transfer.Form990LineId   = lineByCode["24"];  // admin override → must be left alone
+        await db.SaveChangesAsync();
+
+        await DbSeeder.SeedForm990ExpenseLinesAsync(db);
+
+        await db.Entry(visit).ReloadAsync();
+        await db.Entry(missionary).ReloadAsync();
+        await db.Entry(transfer).ReloadAsync();
+        Assert.Equal(lineByCode["17"], visit.Form990LineId);      // corrected 2 → 17
+        Assert.Equal(lineByCode["2"],  missionary.Form990LineId); // corrected 1 → 2
+        Assert.Equal(lineByCode["24"], transfer.Form990LineId);   // admin edit preserved
+    }
 }

API/ROLAC.API.Tests/Services/DisbursementServiceTests.cs

@@ -65,6 +65,8 @@ public class DisbursementServiceTests
         var db = BuildDb(userId);
         db.ChurchProfiles.Add(new ChurchProfile { Id = 1, Name = "ROLAC", NextCheckNumber = 1001 });
         db.Members.Add(new Member { Id = 1, FirstName_en = "John", LastName_en = "Doe", Address = "1 Main St", City = "Arcadia", State = "CA", ZipCode = "91006" });
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 1, Name_en = "Equipment" });
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 2, Name_en = "Food & Beverage" });
         db.SaveChanges();
         var fs = new FakeStorage();
         return (SvcAs(db, fs, userId), db, fs);
@@ -73,8 +75,9 @@ public class DisbursementServiceTests
     private static Expense Approved(string type, decimal amount, int? memberId = null, string? vendor = null) => new()
     {
         Type = type, Status = "Approved", Amount = amount, Description = $"{type} {amount}",
-        MinistryId = 1, CategoryGroupId = 1, SubCategoryId = 1, ExpenseDate = new DateOnly(2026, 6, 1),
+        MinistryId = 1, ExpenseDate = new DateOnly(2026, 6, 1),
         MemberId = memberId, VendorName = vendor,
+        Lines = { new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 1, Amount = amount } },
     };
 
     [Fact]
@@ -97,6 +100,28 @@ public class DisbursementServiceTests
         Assert.Equal("1 Main St", member.Address);
     }
 
+    [Fact]
+    public async Task GroupedWorklist_MultiCategoryExpense_ShowsMultipleLabel()
+    {
+        var (svc, db, _) = Build();
+        db.Expenses.Add(new Expense
+        {
+            Type = "VendorPayment", Status = "Approved", Amount = 50m, Description = "mixed invoice",
+            MinistryId = 1, ExpenseDate = new DateOnly(2026, 6, 1), VendorName = "Costco",
+            Lines =
+            {
+                new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 1, Amount = 30m },
+                new ExpenseLine { CategoryGroupId = 2, SubCategoryId = 2, Amount = 20m },
+            },
+        });
+        await db.SaveChangesAsync();
+
+        var groups = await svc.GetApprovedUnpaidGroupedAsync();
+
+        var line = groups.Single(g => g.PayeeType == "Vendor").Lines.Single();
+        Assert.Equal("Multiple / 多類別", line.CategoryName);
+    }
+
     [Fact]
     public async Task Issue_CreatesOneCheckPerPayee_MarksPaid_SequentialNumbers()
     {

API/ROLAC.API.Tests/Services/ExpenseAiServiceFactoryTests.cs

@@ -0,0 +1,69 @@
+using System.Security.Claims;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Diagnostics;
+using Microsoft.Extensions.Logging.Abstractions;
+using Moq;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.Entities;
+using ROLAC.API.Services.Ai;
+using ROLAC.API.Services.Logging;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class ExpenseAiServiceFactoryTests
+{
+    // ChurchProfile is auditable, so the InMemory store rejects saves unless the
+    // required CreatedBy/UpdatedBy fields are populated. Wire the same audit
+    // interceptor the app uses so seeded entities save cleanly.
+    private static AppDbContext NewDb()
+    {
+        var httpContext = new DefaultHttpContext
+        {
+            User = new ClaimsPrincipal(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, "test-user") })),
+        };
+        var httpContextAccessor = new Mock<IHttpContextAccessor>();
+        httpContextAccessor.Setup(accessor => accessor.HttpContext).Returns(httpContext);
+        return new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .ConfigureWarnings(warnings => warnings.Ignore(InMemoryEventId.TransactionIgnoredWarning))
+            .AddInterceptors(new AuditSaveChangesInterceptor(new CurrentUserAccessor(httpContextAccessor.Object)))
+            .Options);
+    }
+
+    private static ExpenseAiServiceFactory Build(AppDbContext db)
+    {
+        var cfg = new ChurchAiConfigProvider(db);
+        var claude = new ClaudeExpenseAiService(
+            new HttpClient(), cfg, db, NullLogger<ClaudeExpenseAiService>.Instance);
+        var gemini = new GeminiExpenseAiService(
+            new HttpClient(), cfg, db, NullLogger<GeminiExpenseAiService>.Instance);
+        return new ExpenseAiServiceFactory(cfg, claude, gemini);
+    }
+
+    [Fact]
+    public async Task Resolves_Claude_by_default()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", AiProvider = "Claude" });
+        await db.SaveChangesAsync();
+
+        var svc = await Build(db).ResolveAsync();
+
+        Assert.IsType<ClaudeExpenseAiService>(svc);
+    }
+
+    [Fact]
+    public async Task Resolves_Gemini_when_selected()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", AiProvider = "Gemini" });
+        await db.SaveChangesAsync();
+
+        var svc = await Build(db).ResolveAsync();
+
+        Assert.IsType<GeminiExpenseAiService>(svc);
+    }
+}

API/ROLAC.API.Tests/Services/ExpenseCategoryAiServiceFactoryTests.cs

@@ -0,0 +1,69 @@
+using System.Security.Claims;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.EntityFrameworkCore.Diagnostics;
+using Microsoft.Extensions.Logging.Abstractions;
+using Moq;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.Entities;
+using ROLAC.API.Services.Ai;
+using ROLAC.API.Services.Logging;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class ExpenseCategoryAiServiceFactoryTests
+{
+    // ChurchProfile is auditable, so the InMemory store rejects saves unless the
+    // required CreatedBy/UpdatedBy fields are populated. Wire the same audit
+    // interceptor the app uses so seeded entities save cleanly.
+    private static AppDbContext NewDb()
+    {
+        var httpContext = new DefaultHttpContext
+        {
+            User = new ClaimsPrincipal(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, "test-user") })),
+        };
+        var httpContextAccessor = new Mock<IHttpContextAccessor>();
+        httpContextAccessor.Setup(accessor => accessor.HttpContext).Returns(httpContext);
+        return new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .ConfigureWarnings(warnings => warnings.Ignore(InMemoryEventId.TransactionIgnoredWarning))
+            .AddInterceptors(new AuditSaveChangesInterceptor(new CurrentUserAccessor(httpContextAccessor.Object)))
+            .Options);
+    }
+
+    private static ExpenseCategoryAiServiceFactory Build(AppDbContext db)
+    {
+        var cfg = new ChurchAiConfigProvider(db);
+        var claude = new ClaudeExpenseCategoryAiService(
+            new HttpClient(), cfg, db, NullLogger<ClaudeExpenseCategoryAiService>.Instance);
+        var gemini = new GeminiExpenseCategoryAiService(
+            new HttpClient(), cfg, db, NullLogger<GeminiExpenseCategoryAiService>.Instance);
+        return new ExpenseCategoryAiServiceFactory(cfg, claude, gemini);
+    }
+
+    [Fact]
+    public async Task Resolves_Claude_by_default()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", AiProvider = "Claude" });
+        await db.SaveChangesAsync();
+
+        var svc = await Build(db).ResolveAsync();
+
+        Assert.IsType<ClaudeExpenseCategoryAiService>(svc);
+    }
+
+    [Fact]
+    public async Task Resolves_Gemini_when_selected()
+    {
+        using var db = NewDb();
+        db.ChurchProfiles.Add(new ChurchProfile { Name = "C", AiProvider = "Gemini" });
+        await db.SaveChangesAsync();
+
+        var svc = await Build(db).ResolveAsync();
+
+        Assert.IsType<GeminiExpenseCategoryAiService>(svc);
+    }
+}

API/ROLAC.API.Tests/Services/ExpenseServiceTests.cs

@@ -7,8 +7,11 @@ using ROLAC.API.Data;
 using ROLAC.API.Data.Interceptors;
 using ROLAC.API.DTOs.Expense;
 using ROLAC.API.Entities;
+using ROLAC.API.Entities.Logging;
 using ROLAC.API.Services;
+using ROLAC.API.Services.Logging;
 using ROLAC.API.Services.Storage;
+using ROLAC.API.Tests.TestSupport;
 using Xunit;
 
 namespace ROLAC.API.Tests.Services;
@@ -55,6 +58,14 @@ public class ExpenseServiceTests
         return new ExpenseService(db, http.Object, fs, ROLAC.API.Tests.TestSupport.NullAuditLogger.Instance);
     }
 
+    private static ExpenseService SvcAs(AppDbContext db, FakeStorage fs, string userId, IAuditLogger audit)
+    {
+        var http = new Mock<IHttpContextAccessor>();
+        var ctx  = new DefaultHttpContext { User = new(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, userId) })) };
+        http.Setup(x => x.HttpContext).Returns(ctx);
+        return new ExpenseService(db, http.Object, fs, audit);
+    }
+
     // Builds a service whose principal carries ONLY the "sub" claim (no NameIdentifier),
     // mirroring the real JWT (NameClaimType="sub", MapInboundClaims=false).
     private static ExpenseService SvcWithSubClaim(AppDbContext db, FakeStorage fs, string userId)
@@ -67,14 +78,20 @@ public class ExpenseServiceTests
 
     private static CreateExpenseRequest Reimb() => new()
     {
-        Type = "StaffReimbursement", MinistryId = 1, CategoryGroupId = 1, SubCategoryId = 1,
+        Type = "StaffReimbursement", MinistryId = 1,
-        Amount = 45.50m, Description = "Batteries", ExpenseDate = new DateOnly(2026, 5, 28),
+        Lines = { new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 45.50m } },
+        Description = "Batteries", ExpenseDate = new DateOnly(2026, 5, 28),
     };
 
     private static UpdateExpenseRequest CloneToUpdate(CreateExpenseRequest r) => new()
     {
-        Type = r.Type, MinistryId = r.MinistryId, CategoryGroupId = r.CategoryGroupId,
+        Type = r.Type, MinistryId = r.MinistryId,
-        SubCategoryId = r.SubCategoryId, Amount = r.Amount, Description = r.Description,
+        Lines = r.Lines.Select(l => new ExpenseLineInput
+        {
+            CategoryGroupId = l.CategoryGroupId, SubCategoryId = l.SubCategoryId,
+            Amount = l.Amount, FunctionalClass = l.FunctionalClass, Description = l.Description,
+        }).ToList(),
+        Description = r.Description,
         VendorName = r.VendorName, MemberId = r.MemberId, CheckNumber = r.CheckNumber,
         ExpenseDate = r.ExpenseDate, Notes = r.Notes,
     };
@@ -207,7 +224,7 @@ public class ExpenseServiceTests
         Assert.Equal("PendingApproval", (await db.Expenses.FindAsync(id))!.Status);
 
         var edit = CloneToUpdate(Reimb());
-        edit.Amount = 99.99m;
+        edit.Lines[0].Amount = 99.99m;
         await svc.UpdateAsync(id, edit, isFinance: false);
 
         var e = await db.Expenses.FindAsync(id);
@@ -260,13 +277,70 @@ public class ExpenseServiceTests
 
         var id = await svc.CreateAsync(new CreateExpenseRequest
         {
-            Type = "VendorPayment", MinistryId = 1, CategoryGroupId = 1, SubCategoryId = 1,
+            Type = "VendorPayment", MinistryId = 1,
-            Amount = 50m, Description = "x", ExpenseDate = new DateOnly(2026, 5, 1),
+            Lines = { new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 50m, FunctionalClass = "ManagementGeneral" } },
-            FunctionalClass = "ManagementGeneral",
+            Description = "x", ExpenseDate = new DateOnly(2026, 5, 1),
         }, isFinance: true);
 
         var dto = await svc.GetByIdAsync(id);
-        Assert.Equal("ManagementGeneral", dto!.FunctionalClass);
+        Assert.Equal("ManagementGeneral", dto!.Lines.Single().FunctionalClass);
+    }
+
+    [Fact]
+    public async Task Create_MultiLine_SetsHeaderTotal_AndRoundTripsLines()
+    {
+        var (svc, db, _) = Build("u1");
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 2, Name_en = "Food & Beverage" });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 2, GroupId = 2, Name_en = "Snacks" });
+        await db.SaveChangesAsync();
+
+        var r = new CreateExpenseRequest
+        {
+            Type = "VendorPayment", MinistryId = 1, VendorName = "Costco",
+            Description = "Mixed invoice", ExpenseDate = new DateOnly(2026, 5, 1),
+            Lines =
+            {
+                new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 30m },
+                new ExpenseLineInput { CategoryGroupId = 2, SubCategoryId = 2, Amount = 12.50m },
+            },
+        };
+        var id = await svc.CreateAsync(r, isFinance: true);
+
+        Assert.Equal(42.50m, (await db.Expenses.FindAsync(id))!.Amount);
+        var dto = await svc.GetByIdAsync(id);
+        Assert.Equal(2, dto!.Lines.Count);
+        Assert.Equal(42.50m, dto.Amount);
+        Assert.Equal(2, dto.LineCount);
+    }
+
+    [Fact]
+    public async Task Create_WithNoLines_Throws()
+    {
+        var (svc, _, _) = Build("u1");
+        var r = Reimb(); r.Lines.Clear();
+        await Assert.ThrowsAsync<InvalidOperationException>(() => svc.CreateAsync(r, isFinance: false));
+    }
+
+    [Fact]
+    public async Task Update_ReplacesLines_AndRecomputesTotal()
+    {
+        var (svc, db, _) = Build("alice");
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 2, Name_en = "Food & Beverage" });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 2, GroupId = 2, Name_en = "Snacks" });
+        await db.SaveChangesAsync();
+
+        var id = await svc.CreateAsync(Reimb(), isFinance: false);
+
+        var edit = CloneToUpdate(Reimb());
+        edit.Lines = new()
+        {
+            new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 10m },
+            new ExpenseLineInput { CategoryGroupId = 2, SubCategoryId = 2, Amount = 5m },
+        };
+        await svc.UpdateAsync(id, edit, isFinance: false);
+
+        Assert.Equal(15m, (await db.Expenses.FindAsync(id))!.Amount);
+        Assert.Equal(2, await db.ExpenseLines.CountAsync(l => l.ExpenseId == id));
     }
 
     [Fact]
@@ -279,4 +353,93 @@ public class ExpenseServiceTests
         var got = await svc.OpenReceiptAsync(id, isFinance: true);
         Assert.NotNull(got);
     }
+
+    [Fact]
+    public async Task Reject_WritesAuditEntry_WithReason()
+    {
+        var (svc, db, fs) = Build("alice");
+        var id = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(id);
+
+        var audit = new CapturingAuditLogger();
+        await SvcAs(db, fs, "finance", audit).RejectAsync(id, "Receipt unclear, please retake");
+
+        var entry = Assert.Single(audit.Entries);
+        Assert.Equal(AuditActions.ExpenseRejected, entry.Action);
+        Assert.Equal(AuditCategories.Business, entry.Category);
+        Assert.Equal(nameof(ROLAC.API.Entities.Expense), entry.EntityName);
+        Assert.Equal(id.ToString(), entry.EntityId);
+        Assert.Contains("Receipt unclear", entry.Summary);
+    }
+
+    [Fact]
+    public async Task Resubmit_FromRejected_ReturnsToPending_AndClearsReview()
+    {
+        var (svc, db, fs) = Build("alice");
+        var id = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(id);
+        await SvcAs(db, fs, "finance").RejectAsync(id, "Receipt missing");
+
+        // Owner fixes the issue and re-submits.
+        await svc.SubmitAsync(id);
+
+        var e = await db.Expenses.FindAsync(id);
+        Assert.Equal("PendingApproval", e!.Status);
+        Assert.Null(e.ReviewedBy);
+        Assert.Null(e.ReviewedAt);
+        Assert.Null(e.ReviewNotes);
+    }
+
+    [Fact]
+    public async Task Update_OwnRejected_AsNonFinance_Succeeds()
+    {
+        // A rejected reimbursement can be corrected by its owner before re-submitting.
+        var (svc, db, fs) = Build("alice");
+        var id = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(id);
+        await SvcAs(db, fs, "finance").RejectAsync(id, "Amount does not match receipt");
+
+        var edit = CloneToUpdate(Reimb());
+        edit.Lines[0].Amount = 77.77m;
+        await svc.UpdateAsync(id, edit, isFinance: false);
+
+        var e = await db.Expenses.FindAsync(id);
+        Assert.Equal(77.77m, e!.Amount);
+        Assert.Equal("Rejected", e.Status);
+    }
+
+    [Fact]
+    public async Task SaveReceipt_OwnRejected_AsNonFinance_Succeeds()
+    {
+        var (svc, db, fs) = Build("alice");
+        var id = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(id);
+        await SvcAs(db, fs, "finance").RejectAsync(id, "Receipt unclear, please retake");
+
+        using var input = new MemoryStream(Encoding.UTF8.GetBytes("img"));
+        await svc.SaveReceiptAsync(id, input, "retake.jpg", isFinance: false);
+        Assert.NotNull(await svc.OpenReceiptAsync(id, isFinance: true));
+    }
+
+    [Fact]
+    public async Task GetById_ResolvesReviewerName_MemberFullName_EmailFallback()
+    {
+        var (svc, db, fs) = Build("alice");
+        // Reviewer linked to a member → shows the member's full name.
+        db.Members.Add(new Member { Id = 5, FirstName_en = "Sam", LastName_en = "Approver" });
+        db.Users.Add(new AppUser { Id = "reviewer-with-member", MemberId = 5 });
+        // Reviewer with no member → falls back to email.
+        db.Users.Add(new AppUser { Id = "reviewer-no-member", Email = "nomember@church.org" });
+        await db.SaveChangesAsync();
+
+        var withMember = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(withMember);
+        await SvcAs(db, fs, "reviewer-with-member").ApproveAsync(withMember);
+        Assert.Equal("Sam Approver", (await svc.GetByIdAsync(withMember))!.ReviewedByName);
+
+        var noMember = await svc.CreateAsync(Reimb(), isFinance: false);
+        await svc.SubmitAsync(noMember);
+        await SvcAs(db, fs, "reviewer-no-member").RejectAsync(noMember, "Duplicate submission");
+        Assert.Equal("nomember@church.org", (await svc.GetByIdAsync(noMember))!.ReviewedByName);
+    }
 }

API/ROLAC.API.Tests/Services/ExpenseSnapshotServiceTests.cs

@@ -0,0 +1,165 @@
+using System.Security.Claims;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Moq;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.DTOs.Expense;
+using ROLAC.API.Entities;
+using ROLAC.API.Services;
+using ROLAC.API.Services.Logging;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class ExpenseSnapshotServiceTests
+{
+    private static AppDbContext BuildDb(string userId)
+    {
+        var claims = new[] { new Claim(ClaimTypes.NameIdentifier, userId) };
+        var ctx    = new DefaultHttpContext { User = new(new ClaimsIdentity(claims)) };
+        var mock   = new Mock<IHttpContextAccessor>();
+        mock.Setup(x => x.HttpContext).Returns(ctx);
+        return new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .AddInterceptors(new AuditSaveChangesInterceptor(new CurrentUserAccessor(mock.Object))).Options);
+    }
+
+    private static (ExpenseSnapshotService svc, AppDbContext db) Build(string userId = "u1")
+    {
+        var db = BuildDb(userId);
+        db.Ministries.Add(new Ministry { Id = 1, Name_en = "Worship", Name_zh = "敬拜" });
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 1, Name_en = "Facilities" });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 1, GroupId = 1, Name_en = "Rent" });
+        db.SaveChanges();
+
+        var claims = new[] { new Claim(ClaimTypes.NameIdentifier, userId) };
+        var ctx    = new DefaultHttpContext { User = new(new ClaimsIdentity(claims)) };
+        var http   = new Mock<IHttpContextAccessor>();
+        http.Setup(x => x.HttpContext).Returns(ctx);
+        return (new ExpenseSnapshotService(db, http.Object), db);
+    }
+
+    private static CreateExpenseSnapshotRequest Rent() => new()
+    {
+        Name = "Monthly Rent", MinistryId = 1, Description = "Office rent", VendorName = "Landlord X",
+        CheckNumber = "1001",
+        Lines = { new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 1200m } },
+    };
+
+    [Fact]
+    public async Task Create_PersistsHeaderAndLines_StampsCreator()
+    {
+        var (svc, db) = Build("creator-1");
+        var id = await svc.CreateAsync(Rent());
+
+        var saved = await db.ExpenseSnapshots.FindAsync(id);
+        Assert.Equal("Monthly Rent", saved!.Name);
+        Assert.Equal("creator-1", saved.CreatedBy);
+        Assert.Equal(1, await db.ExpenseSnapshotLines.CountAsync(l => l.SnapshotId == id));
+    }
+
+    [Fact]
+    public async Task Create_WithNoLines_Throws()
+    {
+        var (svc, _) = Build();
+        var r = Rent(); r.Lines.Clear();
+        await Assert.ThrowsAsync<InvalidOperationException>(() => svc.CreateAsync(r));
+    }
+
+    [Fact]
+    public async Task Create_WithInvalidFunctionalClass_Throws()
+    {
+        var (svc, _) = Build();
+        var r = Rent();
+        r.Lines[0].FunctionalClass = "NotAClass";
+        await Assert.ThrowsAsync<InvalidOperationException>(() => svc.CreateAsync(r));
+    }
+
+    [Fact]
+    public async Task GetById_ReturnsLines_TotalsAndCreatorName()
+    {
+        var (svc, db) = Build("creator-1");
+        db.Members.Add(new Member { Id = 5, FirstName_en = "Joy", LastName_en = "Wong" });
+        db.Users.Add(new AppUser { Id = "creator-1", MemberId = 5 });
+        await db.SaveChangesAsync();
+
+        var id = await svc.CreateAsync(Rent());
+        var dto = await svc.GetByIdAsync(id);
+
+        Assert.NotNull(dto);
+        Assert.Equal(1200m, dto!.TotalAmount);
+        Assert.Equal(1, dto.LineCount);
+        Assert.Equal("Rent", dto.Lines.Single().SubCategoryName);
+        Assert.Equal("Joy Wong", dto.CreatedByName);
+    }
+
+    [Fact]
+    public async Task GetAll_ReturnsNewestFirst()
+    {
+        var (svc, _) = Build();
+        var first  = await svc.CreateAsync(Rent());
+        var second = await svc.CreateAsync(Rent());
+
+        var all = await svc.GetAllAsync();
+
+        Assert.Equal(2, all.Count);
+        Assert.Equal(second, all[0].Id);
+        Assert.Equal(first,  all[1].Id);
+    }
+
+    [Fact]
+    public async Task Update_RenamesAndReplacesLines()
+    {
+        var (svc, db) = Build();
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 2, Name_en = "Utilities" });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 2, GroupId = 2, Name_en = "Internet" });
+        await db.SaveChangesAsync();
+
+        var id = await svc.CreateAsync(Rent());
+        await svc.UpdateAsync(id, new UpdateExpenseSnapshotRequest
+        {
+            Name = "Monthly Internet", MinistryId = 1, Description = "ISP",
+            Lines = { new ExpenseLineInput { CategoryGroupId = 2, SubCategoryId = 2, Amount = 80m } },
+        });
+
+        var dto = await svc.GetByIdAsync(id);
+        Assert.Equal("Monthly Internet", dto!.Name);
+        Assert.Equal(80m, dto.TotalAmount);
+        Assert.Equal("Internet", dto.Lines.Single().SubCategoryName);
+        Assert.Equal(1, await db.ExpenseSnapshotLines.CountAsync(l => l.SnapshotId == id));
+    }
+
+    [Fact]
+    public async Task Update_MissingId_Throws()
+    {
+        var (svc, _) = Build();
+        await Assert.ThrowsAsync<KeyNotFoundException>(() => svc.UpdateAsync(999, new UpdateExpenseSnapshotRequest
+        {
+            Name = "x", MinistryId = 1, Description = "x",
+            Lines = { new ExpenseLineInput { CategoryGroupId = 1, SubCategoryId = 1, Amount = 1m } },
+        }));
+    }
+
+    [Fact]
+    public async Task Delete_SoftDeletes_HidesFromQueries()
+    {
+        var (svc, db) = Build();
+        var id = await svc.CreateAsync(Rent());
+
+        await svc.DeleteAsync(id);
+
+        Assert.Empty(await svc.GetAllAsync());
+        Assert.Null(await db.ExpenseSnapshots.FirstOrDefaultAsync(s => s.Id == id));
+    }
+
+    [Fact]
+    public async Task Delete_StampsDeletedBy()
+    {
+        var (svc, db) = Build("deleter-1");
+        var id = await svc.CreateAsync(Rent());
+        await svc.DeleteAsync(id);
+        var row = await db.ExpenseSnapshots.IgnoreQueryFilters().FirstAsync(s => s.Id == id);
+        Assert.Equal("deleter-1", row.DeletedBy);
+    }
+}

API/ROLAC.API.Tests/Services/Form1099FormServiceTests.cs

@@ -0,0 +1,73 @@
+using System.Globalization;
+using System.Text;
+using ROLAC.API.DTOs.Finance;
+using ROLAC.API.Services;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class Form1099FormServiceTests
+{
+    /// <summary>Stub report service: only GetAnnualSummaryAsync is exercised by the CSV export.</summary>
+    private sealed class StubReportService : IForm1099ReportService
+    {
+        private readonly Form1099SummaryDto _summary;
+        public StubReportService(Form1099SummaryDto summary) => _summary = summary;
+
+        public Task<Form1099SummaryDto> GetAnnualSummaryAsync(int taxYear) => Task.FromResult(_summary);
+        public Task<List<Form1099BoxDto>> GetBoxesAsync() => throw new NotImplementedException();
+        public Task<Form1099RecipientDetailDto?> GetRecipientDetailAsync(int payeeId, int taxYear)
+            => throw new NotImplementedException();
+    }
+
+    private static Form1099FormService BuildService(Form1099SummaryDto summary) =>
+        // IPayee1099Service and AppDbContext are only used by RenderCopyBAsync, not by the CSV path.
+        new Form1099FormService(new StubReportService(summary), payees: null!, db: null!);
+
+    [Fact]
+    public async Task ExportFilingCsvAsync_WritesHeaderRowPerRecipientAndInvariantNumbers()
+    {
+        var summary = new Form1099SummaryDto
+        {
+            TaxYear = 2026,
+            Rows =
+            {
+                new Form1099RecipientRowDto
+                {
+                    PayeeId = 1, LegalName = "Acme, LLC", TinLast4 = "1234", W9Status = "OnFile",
+                    NecTotal = 1234.50m, RentsTotal = 0m, GrandTotal = 1234.50m, MeetsThreshold = true
+                },
+                new Form1099RecipientRowDto
+                {
+                    PayeeId = 2, LegalName = "Bob Smith", TinLast4 = "9876", W9Status = "Missing",
+                    NecTotal = 100m, RentsTotal = 50m, GrandTotal = 150m, MeetsThreshold = false
+                },
+            }
+        };
+
+        var service = BuildService(summary);
+        var (stream, contentType, fileName) = await service.ExportFilingCsvAsync(2026);
+
+        Assert.Equal("text/csv", contentType);
+        Assert.Equal("1099-filing-2026.csv", fileName);
+
+        using var reader = new StreamReader(stream, Encoding.UTF8);
+        var text = await reader.ReadToEndAsync();
+        var lines = text.Split(new[] { "\r\n", "\n" }, StringSplitOptions.RemoveEmptyEntries);
+
+        // Header + one data line per row.
+        Assert.Equal(3, lines.Length);
+        Assert.Equal("LegalName,TinLast4,W9Status,Box1_NEC,Box1_Rents,Total,MeetsThreshold", lines[0]);
+
+        // A value containing a comma is quoted.
+        Assert.StartsWith("\"Acme, LLC\",1234,OnFile,", lines[1]);
+
+        // Invariant numeric formatting (period decimal separator) and Y/N threshold flag.
+        Assert.Contains("1234.50", lines[1]);
+        Assert.EndsWith(",Y", lines[1]);
+        Assert.EndsWith(",N", lines[2]);
+
+        // Sanity: the period really is the invariant separator regardless of current culture.
+        Assert.Equal("1234.50", 1234.50m.ToString(CultureInfo.InvariantCulture));
+    }
+}

API/ROLAC.API.Tests/Services/Form1099ReportServiceTests.cs

@@ -0,0 +1,106 @@
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Moq;
+using System.Security.Claims;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.Entities;
+using ROLAC.API.Services;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class Form1099ReportServiceTests
+{
+    private static AppDbContext NewDb()
+    {
+        var httpContext = new DefaultHttpContext { User = new(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, "t") })) };
+        var accessorMock = new Mock<IHttpContextAccessor>();
+        accessorMock.Setup(x => x.HttpContext).Returns(httpContext);
+        return new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .AddInterceptors(new AuditSaveChangesInterceptor(new ROLAC.API.Services.Logging.CurrentUserAccessor(accessorMock.Object))).Options);
+    }
+
+    private static AppDbContext Seeded(out int necSubId, out int rentSubId, out int salarySubId)
+    {
+        var db = NewDb();
+        db.Ministries.Add(new Ministry { Id = 1, Name_en = "Admin", DefaultFunctionalClass = "Program" });
+        var nec  = new Form1099Box { Id = 1, BoxCode = Form1099.BoxNec1,  Name_en = "NEC",  FormType = "1099-NEC",  SortOrder = 1 };
+        var rent = new Form1099Box { Id = 2, BoxCode = Form1099.BoxMisc1, Name_en = "Rent", FormType = "1099-MISC", SortOrder = 2 };
+        db.Form1099Boxes.AddRange(nec, rent);
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 1, Name_en = "Personnel" });
+        db.ExpenseCategoryGroups.Add(new ExpenseCategoryGroup { Id = 2, Name_en = "Facility" });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 1, GroupId = 1, Name_en = "Contract Labor", Form1099BoxId = 1 });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 2, GroupId = 2, Name_en = "Rent",           Form1099BoxId = 2 });
+        db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 3, GroupId = 1, Name_en = "Salary & Wages", Form1099BoxId = null });
+        db.SaveChanges();
+        necSubId = 1; rentSubId = 2; salarySubId = 3;
+        return db;
+    }
+
+    private static void AddPaidExpense(AppDbContext db, int payeeId, int subId, int groupId, decimal amount, DateOnly paidOn)
+    {
+        var e = new Expense
+        {
+            MinistryId = 1, Type = "VendorPayment", Status = "Paid", PayeeId = payeeId,
+            Amount = amount, Description = "x", ExpenseDate = paidOn,
+            PaidAt = new DateTimeOffset(paidOn.ToDateTime(TimeOnly.MinValue), TimeSpan.Zero),
+            Lines = [ new ExpenseLine { CategoryGroupId = groupId, SubCategoryId = subId, Amount = amount } ],
+        };
+        db.Expenses.Add(e);
+        db.SaveChanges();
+    }
+
+    [Fact]
+    public async Task Sums_tracked_recipient_by_box_and_flags_threshold_and_w9()
+    {
+        var db = Seeded(out var necSub, out var rentSub, out _);
+        db.Payee1099s.Add(new Payee1099 { Id = 10, LegalName = "Pat Player", Is1099Tracked = true, W9Status = "Missing" });
+        db.SaveChanges();
+        AddPaidExpense(db, 10, necSub, 1, 700m, new DateOnly(2026, 3, 1));
+        AddPaidExpense(db, 10, rentSub, 2, 500m, new DateOnly(2026, 4, 1));
+
+        var svc = new Form1099ReportService(db);
+        var sum = await svc.GetAnnualSummaryAsync(2026);
+
+        var row = Assert.Single(sum.Rows);
+        Assert.Equal(700m, row.NecTotal);
+        Assert.Equal(500m, row.RentsTotal);
+        Assert.Equal(1200m, row.GrandTotal);
+        Assert.True(row.MeetsThreshold);
+        Assert.True(row.W9Missing);
+        Assert.Equal(1, sum.RecipientsAtThreshold);
+        Assert.Equal(1, sum.RecipientsMissingW9);
+    }
+
+    [Fact]
+    public async Task Excludes_untracked_recipients_and_unmapped_and_wrong_year()
+    {
+        var db = Seeded(out var necSub, out _, out var salarySub);
+        db.Payee1099s.Add(new Payee1099 { Id = 10, LegalName = "Tracked Tim", Is1099Tracked = true, W9Status = "OnFile" });
+        db.Payee1099s.Add(new Payee1099 { Id = 11, LegalName = "Corp Inc",    Is1099Tracked = false, W9Status = "OnFile" });
+        db.SaveChanges();
+        AddPaidExpense(db, 11, necSub,    1, 5000m, new DateOnly(2026, 5, 1)); // untracked
+        AddPaidExpense(db, 10, salarySub, 1, 5000m, new DateOnly(2026, 6, 1)); // unmapped box
+        AddPaidExpense(db, 10, necSub,    1, 5000m, new DateOnly(2025, 6, 1)); // wrong year
+
+        var sum = await new Form1099ReportService(db).GetAnnualSummaryAsync(2026);
+        Assert.Empty(sum.Rows);
+    }
+
+    [Fact]
+    public async Task Threshold_flag_is_false_below_600()
+    {
+        var db = Seeded(out var necSub, out _, out _);
+        db.Payee1099s.Add(new Payee1099 { Id = 10, LegalName = "Small Sam", Is1099Tracked = true, W9Status = "OnFile" });
+        db.SaveChanges();
+        AddPaidExpense(db, 10, necSub, 1, 599.99m, new DateOnly(2026, 7, 1));
+
+        var sum = await new Form1099ReportService(db).GetAnnualSummaryAsync(2026);
+        var row = Assert.Single(sum.Rows);
+        Assert.False(row.MeetsThreshold);
+        Assert.False(row.W9Missing);
+        Assert.Equal(0, sum.RecipientsAtThreshold);
+    }
+}

API/ROLAC.API.Tests/Services/Form990ReportServiceTests.cs

@@ -36,9 +36,9 @@ public class Form990ReportServiceTests
 
     private static Expense Exp(int min, int sub, decimal amt, string status, string? fc = null) => new()
     {
-        MinistryId = min, CategoryGroupId = 1, SubCategoryId = sub, Type = "VendorPayment",
+        MinistryId = min, Type = "VendorPayment",
         Status = status, Amount = amt, Description = "x", ExpenseDate = new DateOnly(2026, 5, 10),
-        FunctionalClass = fc,
+        Lines = { new ExpenseLine { CategoryGroupId = 1, SubCategoryId = sub, Amount = amt, FunctionalClass = fc } },
     };
 
     [Fact]
@@ -82,4 +82,31 @@ public class Form990ReportServiceTests
         var stmt = await svc.GetFunctionalExpenseStatementAsync(new DateOnly(2026, 5, 1), new DateOnly(2026, 5, 31));
         Assert.Equal(100m, stmt.GrandTotal);
     }
+
+    [Fact]
+    public async Task Statement_SplitsOneExpenseAcrossLines()
+    {
+        // One invoice with two lines of different categories must land on two different 990 lines.
+        using var db = BuildDb();
+        await SeedAsync(db);
+        db.Expenses.Add(new Expense
+        {
+            MinistryId = 2, Type = "VendorPayment", Status = "Paid", Amount = 70m,
+            Description = "mixed", ExpenseDate = new DateOnly(2026, 5, 10),
+            Lines =
+            {
+                new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 1, Amount = 50m }, // sub→line 7
+                new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 2, Amount = 20m }, // sub unmapped→group fallback line 24
+            },
+        });
+        await db.SaveChangesAsync();
+        var svc = new Form990ReportService(db);
+
+        var stmt = await svc.GetFunctionalExpenseStatementAsync(null, null);
+
+        Assert.Equal(50m, stmt.Rows.Single(r => r.LineCode == "7").Program);   // ministry 2 default = Program
+        Assert.Equal(20m, stmt.Rows.Single(r => r.LineCode == "24").Program);
+        Assert.Equal(70m, stmt.GrandTotal);
+        Assert.Equal(1,   stmt.UnmappedExpenseCount);                          // one unmapped line
+    }
 }

API/ROLAC.API.Tests/Services/MonthlyStatementServiceTests.cs

@@ -42,8 +42,8 @@ public class MonthlyStatementServiceTests
         db.ExpenseSubCategories.Add(new ExpenseSubCategory { Id = 1, GroupId = 1, Name_en = "Misc" });
         db.Givings.Add(new Giving { GivingCategoryId = 1, Amount = 1000m, PaymentMethod = "Cash", GivingDate = new DateOnly(2026, 5, 10) });
         db.Givings.Add(new Giving { GivingCategoryId = 1, Amount = 500m,  PaymentMethod = "Cash", GivingDate = new DateOnly(2026, 6, 1) });
-        db.Expenses.Add(new Expense { MinistryId = 1, CategoryGroupId = 1, SubCategoryId = 1, Type = "VendorPayment", Status = "Paid", Amount = 300m, Description = "x", ExpenseDate = new DateOnly(2026, 5, 20) });
+        db.Expenses.Add(new Expense { MinistryId = 1, Type = "VendorPayment", Status = "Paid", Amount = 300m, Description = "x", ExpenseDate = new DateOnly(2026, 5, 20), Lines = { new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 1, Amount = 300m } } });
-        db.Expenses.Add(new Expense { MinistryId = 1, CategoryGroupId = 1, SubCategoryId = 1, Type = "StaffReimbursement", Status = "Approved", Amount = 999m, Description = "not paid", ExpenseDate = new DateOnly(2026, 5, 21) });
+        db.Expenses.Add(new Expense { MinistryId = 1, Type = "StaffReimbursement", Status = "Approved", Amount = 999m, Description = "not paid", ExpenseDate = new DateOnly(2026, 5, 21), Lines = { new ExpenseLine { CategoryGroupId = 1, SubCategoryId = 1, Amount = 999m } } });
         await db.SaveChangesAsync();
         var svc = Build(db);
 

API/ROLAC.API.Tests/Services/Payee1099ServiceTests.cs

@@ -0,0 +1,112 @@
+using Microsoft.AspNetCore.DataProtection;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using Moq;
+using System.Security.Claims;
+using ROLAC.API.Data;
+using ROLAC.API.Data.Interceptors;
+using ROLAC.API.DTOs.Payee;
+using ROLAC.API.Entities;
+using ROLAC.API.Services;
+using ROLAC.API.Services.Logging;
+using ROLAC.API.Services.Security;
+using ROLAC.API.Services.Storage;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class Payee1099ServiceTests
+{
+    // Minimal in-memory IFileStorage (mirrors the ExpenseServiceTests fake).
+    private sealed class FakeStorage : IFileStorage
+    {
+        public Dictionary<string, byte[]> Files = new();
+        public Task<string> SaveAsync(Stream c, string p, CancellationToken ct = default)
+        { using var ms = new MemoryStream(); c.CopyTo(ms); Files[p] = ms.ToArray(); return Task.FromResult(p); }
+        public Task<Stream?> OpenReadAsync(string p, CancellationToken ct = default)
+        => Task.FromResult<Stream?>(Files.TryGetValue(p, out var b) ? new MemoryStream(b) : null);
+        public Task DeleteAsync(string p, CancellationToken ct = default) { Files.Remove(p); return Task.CompletedTask; }
+    }
+
+    private static (Payee1099Service svc, AppDbContext db) Build()
+    {
+        var httpContext = new DefaultHttpContext { User = new(new ClaimsIdentity(new[] { new Claim(ClaimTypes.NameIdentifier, "test-user") })) };
+        var accessorMock = new Mock<IHttpContextAccessor>();
+        accessorMock.Setup(x => x.HttpContext).Returns(httpContext);
+        var db = new AppDbContext(new DbContextOptionsBuilder<AppDbContext>()
+            .UseInMemoryDatabase(Guid.NewGuid().ToString())
+            .AddInterceptors(new AuditSaveChangesInterceptor(new CurrentUserAccessor(accessorMock.Object))).Options);
+        var tin = new TinProtector(DataProtectionProvider.Create("ROLAC.Tests"));
+        return (new Payee1099Service(db, tin, new FakeStorage()), db);
+    }
+
+    [Fact]
+    public async Task Create_encrypts_tin_and_stores_last4_only_in_clear()
+    {
+        var (svc, db) = Build();
+        var id = await svc.CreateAsync(new SavePayee1099Request
+        { LegalName = "Pat Player", TinType = "SSN", Tin = "123-45-6789", W9Status = "OnFile" });
+
+        var saved = await db.Payee1099s.FindAsync(id);
+        Assert.NotNull(saved);
+        Assert.Equal("6789", saved!.TinLast4);
+        Assert.NotNull(saved.TinEncrypted);
+        Assert.DoesNotContain("123-45-6789", saved.TinEncrypted!);
+        Assert.Equal("123-45-6789", await svc.RevealTinAsync(id));
+    }
+
+    [Fact]
+    public async Task Update_with_null_tin_keeps_existing_ciphertext()
+    {
+        var (svc, db) = Build();
+        var id = await svc.CreateAsync(new SavePayee1099Request { LegalName = "X", Tin = "11-2223333" });
+        var before = (await db.Payee1099s.FindAsync(id))!.TinEncrypted;
+
+        await svc.UpdateAsync(id, new SavePayee1099Request { LegalName = "X renamed", Tin = null });
+
+        var after = await db.Payee1099s.FindAsync(id);
+        Assert.Equal("X renamed", after!.LegalName);
+        Assert.Equal(before, after.TinEncrypted);
+        Assert.Equal("3333", after.TinLast4);
+    }
+
+    [Fact]
+    public async Task List_dto_masks_tin_to_last4()
+    {
+        var (svc, _) = Build();
+        await svc.CreateAsync(new SavePayee1099Request { LegalName = "Y", Tin = "999-88-7777" });
+        var list = await svc.GetAllAsync(includeInactive: true);
+        var item = Assert.Single(list);
+        Assert.Equal("7777", item.TinLast4);
+    }
+
+    [Fact]
+    public async Task Delete_is_soft_and_hides_from_list()
+    {
+        var (svc, _) = Build();
+        var id = await svc.CreateAsync(new SavePayee1099Request { LegalName = "Z" });
+        await svc.DeleteAsync(id);
+        Assert.Empty(await svc.GetAllAsync(includeInactive: true));
+    }
+
+    [Fact]
+    public async Task SaveW9_records_document_and_round_trips_bytes()
+    {
+        var (svc, _) = Build();
+        var id = await svc.CreateAsync(new SavePayee1099Request { LegalName = "W9 Payee" });
+
+        var bytes = new byte[] { 1, 2, 3, 4, 5 };
+        await svc.SaveW9Async(id, new MemoryStream(bytes), "w9.pdf");
+
+        var dto = await svc.GetByIdAsync(id);
+        Assert.NotNull(dto);
+        Assert.True(dto!.HasW9Document);
+
+        var opened = await svc.OpenW9Async(id);
+        Assert.NotNull(opened);
+        Assert.Equal("application/pdf", opened!.Value.contentType);
+        using var ms = new MemoryStream();
+        await opened.Value.stream.CopyToAsync(ms);
+        Assert.Equal(bytes, ms.ToArray());
+    }
+}

API/ROLAC.API.Tests/Services/TinProtectorTests.cs

@@ -0,0 +1,30 @@
+using Microsoft.AspNetCore.DataProtection;
+using ROLAC.API.Services.Security;
+using Xunit;
+
+namespace ROLAC.API.Tests.Services;
+
+public class TinProtectorTests
+{
+    private static TinProtector Build() =>
+        new TinProtector(DataProtectionProvider.Create("ROLAC.Tests"));
+
+    [Fact]
+    public void Protect_then_Unprotect_round_trips()
+    {
+        var p = Build();
+        var cipher = p.Protect("123-45-6789");
+        Assert.NotEqual("123-45-6789", cipher);
+        Assert.Equal("123-45-6789", p.Unprotect(cipher));
+    }
+
+    [Theory]
+    [InlineData("123-45-6789", "6789")]
+    [InlineData("12-3456789",  "6789")]
+    [InlineData("7", "7")]
+    public void Last4_keeps_only_trailing_digits(string raw, string expected)
+        => Assert.Equal(expected, TinProtector.Last4(raw));
+
+    [Fact]
+    public void Last4_of_null_is_null() => Assert.Null(TinProtector.Last4(null));
+}

API/ROLAC.API.Tests/TestSupport/CapturingAuditLogger.cs

@@ -0,0 +1,21 @@
+using ROLAC.API.Entities.Logging;
+using ROLAC.API.Services.Logging;
+
+namespace ROLAC.API.Tests.TestSupport;
+
+/// <summary>Records every audit Write so tests can assert on the emitted actions/summaries.</summary>
+public sealed class CapturingAuditLogger : IAuditLogger
+{
+    public readonly record struct Entry(string Action, string Category, string? EntityName, string? EntityId, string? Summary);
+
+    public readonly List<Entry> Entries = new();
+
+    public void Write(
+        string action, string category, LogLevelEnum level = LogLevelEnum.Information,
+        string? entityName = null, string? entityId = null, string? summary = null,
+        object? before = null, object? after = null,
+        string? userId = null, string? userEmail = null, string? ipAddress = null)
+    {
+        Entries.Add(new Entry(action, category, entityName, entityId, summary));
+    }
+}

API/ROLAC.API/Authorization/Modules.cs

@@ -17,6 +17,7 @@ public static class Modules
     public const string Ministries        = "Ministries";
     public const string FinanceDashboard  = "FinanceDashboard";
     public const string Form990Report     = "Form990Report";
+    public const string Form1099          = "Form1099";
     public const string MonthlyStatements = "MonthlyStatements";
     public const string ChurchProfile     = "ChurchProfile";
     public const string Disbursements     = "Disbursements";
@@ -39,6 +40,7 @@ public static class Modules
         Ministries,
         FinanceDashboard,
         Form990Report,
+        Form1099,
         MonthlyStatements,
         ChurchProfile,
         Disbursements,

API/ROLAC.API/Controllers/ExpenseAiController.cs

@@ -0,0 +1,27 @@
+using Microsoft.AspNetCore.Authorization;
+using Microsoft.AspNetCore.Mvc;
+using ROLAC.API.DTOs.Expense;
+using ROLAC.API.Services.Ai;
+
+namespace ROLAC.API.Controllers;
+
+[ApiController]
+[Route("api/expense-ai")]
+[Authorize]   // Open to any authenticated user — same audience as the expense-entry form, which any
+              // member filing a reimbursement can reach. The endpoint only reads the category catalog.
+public class ExpenseAiController : ControllerBase
+{
+    private readonly IExpenseAiServiceFactory _factory;
+    public ExpenseAiController(IExpenseAiServiceFactory factory) => _factory = factory;
+
+    [HttpPost("assist")]
+    public async Task<IActionResult> Assist([FromBody] ExpenseAiAssistRequest request, CancellationToken ct)
+    {
+        if (string.IsNullOrWhiteSpace(request.Text))
+            return BadRequest("Text is required.");
+
+        var svc = await _factory.ResolveAsync(ct);
+        var suggestion = await svc.SuggestAsync(request.Text, request.Amount, ct);
+        return Ok(suggestion);
+    }
+}

API/ROLAC.API/Controllers/ExpenseCategoriesController.cs

@@ -3,6 +3,7 @@ using Microsoft.AspNetCore.Mvc;
 using ROLAC.API.Authorization;
 using ROLAC.API.DTOs.Expense;
 using ROLAC.API.Services;
+using ROLAC.API.Services.Ai;
 
 namespace ROLAC.API.Controllers;
 
@@ -13,12 +14,30 @@ namespace ROLAC.API.Controllers;
 public class ExpenseCategoriesController : ControllerBase
 {
     private readonly IExpenseCategoryService _svc;
-    public ExpenseCategoriesController(IExpenseCategoryService svc) => _svc = svc;
+    private readonly IExpenseCategoryAiServiceFactory _aiFactory;
+    public ExpenseCategoriesController(IExpenseCategoryService svc, IExpenseCategoryAiServiceFactory aiFactory)
+    {
+        _svc = svc;
+        _aiFactory = aiFactory;
+    }
 
     [HttpGet]
     public async Task<IActionResult> GetAll([FromQuery] bool includeInactive = false)
         => Ok(await _svc.GetAllAsync(includeInactive));
 
+    // Suggest an English name + Form 990 line for a category being defined. Write-gated: category
+    // editing is finance/admin-only, unlike the member-facing expense-ai/assist endpoint.
+    [HttpPost("ai-suggest")]
+    [HasPermission(Modules.ExpenseCategories, PermissionActions.Write)]
+    public async Task<IActionResult> AiSuggest([FromBody] ExpenseCategoryAiRequest r, CancellationToken ct)
+    {
+        if (string.IsNullOrWhiteSpace(r.Name_zh) && string.IsNullOrWhiteSpace(r.Name_en))
+            return BadRequest("A name is required.");
+
+        var svc = await _aiFactory.ResolveAsync(ct);
+        return Ok(await svc.SuggestAsync(r, ct));
+    }
+
     [HttpPost("groups")]
     [HasPermission(Modules.ExpenseCategories, PermissionActions.Write)]
     public async Task<IActionResult> CreateGroup([FromBody] CreateExpenseGroupRequest r)

API/ROLAC.API/Controllers/ExpenseSnapshotsController.cs

@@ -0,0 +1,68 @@
+using Microsoft.AspNetCore.Authorization;
+using Microsoft.AspNetCore.Mvc;
+using ROLAC.API.Authorization;
+using ROLAC.API.DTOs.Expense;
+using ROLAC.API.Services;
+
+namespace ROLAC.API.Controllers;
+
+// Snapshots are reusable vendor-payment templates — a finance tool. Every action requires
+// Expenses:Write (super_admin bypasses), matching who can create vendor payments.
+[ApiController]
+[Route("api/expense-snapshots")]
+[Authorize]
+public class ExpenseSnapshotsController : ControllerBase
+{
+    private readonly IExpenseSnapshotService _svc;
+    private readonly IPermissionService _perms;
+    public ExpenseSnapshotsController(IExpenseSnapshotService svc, IPermissionService perms)
+    {
+        _svc = svc;
+        _perms = perms;
+    }
+
+    private List<string> Roles() => User.FindAll("role").Select(claim => claim.Value).ToList();
+    private bool IsSuperAdmin() => User.IsInRole(PermissionAuthorizationHandler.SuperAdminRole);
+    private async Task<bool> CanManageAsync() =>
+        IsSuperAdmin() || await _perms.HasPermissionAsync(Roles(), Modules.Expenses, PermissionActions.Write);
+
+    [HttpGet]
+    public async Task<IActionResult> GetAll()
+    {
+        if (!await CanManageAsync()) return Forbid();
+        return Ok(await _svc.GetAllAsync());
+    }
+
+    [HttpGet("{id:int}")]
+    public async Task<IActionResult> GetById(int id)
+    {
+        if (!await CanManageAsync()) return Forbid();
+        var dto = await _svc.GetByIdAsync(id);
+        return dto is null ? NotFound() : Ok(dto);
+    }
+
+    [HttpPost]
+    public async Task<IActionResult> Create([FromBody] CreateExpenseSnapshotRequest r)
+    {
+        if (!await CanManageAsync()) return Forbid();
+        try { return Ok(new { id = await _svc.CreateAsync(r) }); }
+        catch (InvalidOperationException ex) { return Conflict(new { message = ex.Message }); }
+    }
+
+    [HttpPut("{id:int}")]
+    public async Task<IActionResult> Update(int id, [FromBody] UpdateExpenseSnapshotRequest r)
+    {
+        if (!await CanManageAsync()) return Forbid();
+        try { await _svc.UpdateAsync(id, r); return NoContent(); }
+        catch (KeyNotFoundException) { return NotFound(); }
+        catch (InvalidOperationException ex) { return Conflict(new { message = ex.Message }); }
+    }
+
+    [HttpDelete("{id:int}")]
+    public async Task<IActionResult> Delete(int id)
+    {
+        if (!await CanManageAsync()) return Forbid();
+        try { await _svc.DeleteAsync(id); return NoContent(); }
+        catch (KeyNotFoundException) { return NotFound(); }
+    }
+}

API/ROLAC.API/Controllers/Form1099ReportController.cs

@@ -0,0 +1,44 @@
+using Microsoft.AspNetCore.Mvc;
+using ROLAC.API.Authorization;
+using ROLAC.API.Services;
+
+namespace ROLAC.API.Controllers;
+
+[ApiController]
+[Route("api/form1099-report")]
+[HasPermission(Modules.Form1099, PermissionActions.Read)]
+public class Form1099ReportController : ControllerBase
+{
+    private readonly IForm1099ReportService _svc;
+    private readonly I1099FormService _form;
+    public Form1099ReportController(IForm1099ReportService svc, I1099FormService form)
+    {
+        _svc = svc;
+        _form = form;
+    }
+
+    [HttpGet("boxes")]
+    public async Task<IActionResult> Boxes() => Ok(await _svc.GetBoxesAsync());
+
+    [HttpGet("summary")]
+    public async Task<IActionResult> Summary([FromQuery] int taxYear)
+        => Ok(await _svc.GetAnnualSummaryAsync(taxYear));
+
+    [HttpGet("recipient/{payeeId:int}")]
+    public async Task<IActionResult> Recipient(int payeeId, [FromQuery] int taxYear)
+        => await _svc.GetRecipientDetailAsync(payeeId, taxYear) is { } d ? Ok(d) : NotFound();
+
+    [HttpGet("recipient/{payeeId:int}/copy-b")]
+    public async Task<IActionResult> CopyB(int payeeId, [FromQuery] int taxYear)
+    {
+        var (stream, contentType, fileName) = await _form.RenderCopyBAsync(payeeId, taxYear);
+        return File(stream, contentType, fileName);
+    }
+
+    [HttpGet("export-csv")]
+    public async Task<IActionResult> ExportCsv([FromQuery] int taxYear)
+    {
+        var (stream, contentType, fileName) = await _form.ExportFilingCsvAsync(taxYear);
+        return File(stream, contentType, fileName);
+    }
+}

API/ROLAC.API/Controllers/Payee1099Controller.cs

@@ -0,0 +1,71 @@
+using Microsoft.AspNetCore.Mvc;
+using ROLAC.API.Authorization;
+using ROLAC.API.DTOs.Payee;
+using ROLAC.API.Services;
+
+namespace ROLAC.API.Controllers;
+
+[ApiController]
+[Route("api/payee-1099")]
+[HasPermission(Modules.Form1099, PermissionActions.Read)]
+public class Payee1099Controller : ControllerBase
+{
+    private readonly IPayee1099Service _svc;
+    public Payee1099Controller(IPayee1099Service svc) => _svc = svc;
+
+    [HttpGet]
+    public async Task<IActionResult> GetAll([FromQuery] bool includeInactive = false)
+        => Ok(await _svc.GetAllAsync(includeInactive));
+
+    [HttpGet("{id:int}")]
+    public async Task<IActionResult> GetById(int id)
+        => await _svc.GetByIdAsync(id) is { } dto ? Ok(dto) : NotFound();
+
+    [HttpPost]
+    [HasPermission(Modules.Form1099, PermissionActions.Write)]
+    public async Task<IActionResult> Create([FromBody] SavePayee1099Request r)
+        => Ok(new { id = await _svc.CreateAsync(r) });
+
+    [HttpPut("{id:int}")]
+    [HasPermission(Modules.Form1099, PermissionActions.Write)]
+    public async Task<IActionResult> Update(int id, [FromBody] SavePayee1099Request r)
+    { await _svc.UpdateAsync(id, r); return NoContent(); }
+
+    [HttpDelete("{id:int}")]
+    [HasPermission(Modules.Form1099, PermissionActions.Delete)]
+    public async Task<IActionResult> Delete(int id)
+    { await _svc.DeleteAsync(id); return NoContent(); }
+
+    // Full TIN reveal is gated on Write (a stronger right than Read).
+    [HttpGet("{id:int}/tin")]
+    [HasPermission(Modules.Form1099, PermissionActions.Write)]
+    public async Task<IActionResult> RevealTin(int id)
+        => Ok(new { tin = await _svc.RevealTinAsync(id) });
+
+    // Mirrors the expense-receipt upload: multipart form file, size-limited, type-checked.
+    [HttpPost("{id:int}/w9")]
+    [HasPermission(Modules.Form1099, PermissionActions.Write)]
+    [RequestSizeLimit(10_485_760)]
+    public async Task<IActionResult> UploadW9(int id, IFormFile file)
+    {
+        if (file is null || file.Length == 0) return BadRequest(new { message = "No file." });
+        var allowed = new[] { "image/jpeg", "image/png", "image/webp", "application/pdf" };
+        if (!allowed.Contains(file.ContentType)) return BadRequest(new { message = "Unsupported file type." });
+        try
+        {
+            await using var stream = file.OpenReadStream();
+            await _svc.SaveW9Async(id, stream, file.FileName);
+            return NoContent();
+        }
+        catch (KeyNotFoundException) { return NotFound(); }
+    }
+
+    // Class-level Read gate covers viewing the stored W-9 (mirrors the receipt GET).
+    [HttpGet("{id:int}/w9")]
+    public async Task<IActionResult> GetW9(int id)
+    {
+        var result = await _svc.OpenW9Async(id);
+        if (result is null) return NotFound();
+        return File(result.Value.stream, result.Value.contentType);
+    }
+}

API/ROLAC.API/DTOs/Disbursement/ChurchProfileDtos.cs

@@ -16,7 +16,13 @@ public class ChurchProfileDto
     public string? BankName          { get; set; }
     public string? BankAccountNumber { get; set; }
     public string? BankRoutingNumber { get; set; }
+    public string? PayerEin          { get; set; }
     public int     NextCheckNumber   { get; set; }
+    public string  AiProvider         { get; set; } = "Claude";
+    public string? ClaudeModel        { get; set; }
+    public string? ClaudeApiKeyMasked { get; set; }
+    public string? GeminiModel        { get; set; }
+    public string? GeminiApiKeyMasked { get; set; }
 }
 
 public class UpdateChurchProfileRequest
@@ -33,5 +39,11 @@ public class UpdateChurchProfileRequest
     [MaxLength(200)] public string? BankName { get; set; }
     [MaxLength(50)]  public string? BankAccountNumber { get; set; }
     [MaxLength(50)]  public string? BankRoutingNumber { get; set; }
+    [MaxLength(20)]  public string? PayerEin          { get; set; }
     [Range(1, int.MaxValue)] public int NextCheckNumber { get; set; }
+    [MaxLength(20)]  public string  AiProvider   { get; set; } = "Claude";
+    [MaxLength(100)] public string? ClaudeModel  { get; set; }
+    [MaxLength(500)] public string? ClaudeApiKey { get; set; }   // null/blank = leave unchanged
+    [MaxLength(100)] public string? GeminiModel  { get; set; }
+    [MaxLength(500)] public string? GeminiApiKey { get; set; }   // null/blank = leave unchanged
 }

API/ROLAC.API/DTOs/Expense/ExpenseAiDtos.cs

@@ -0,0 +1,65 @@
+using System.ComponentModel.DataAnnotations;
+namespace ROLAC.API.DTOs.Expense;
+
+/// <summary>Request body for the expense AI assist endpoint.</summary>
+public class ExpenseAiAssistRequest
+{
+    /// <summary>The user's free-text expense description (typically Chinese).</summary>
+    [Required] public string Text { get; set; } = "";
+    /// <summary>The expense amount, used as a hint when classifying the category.</summary>
+    public decimal Amount { get; set; }
+}
+
+/// <summary>
+/// AI suggestion for an expense: an English translation of the description plus a proposed
+/// major category (大項) and sub-category (系項). Category ids are null when the model could
+/// not confidently classify or returned an id outside the live catalog.
+/// </summary>
+public class ExpenseAiSuggestion
+{
+    public string? EnglishDescription { get; set; }
+    /// <summary>Typo-corrected, refined Traditional Chinese description.</summary>
+    public string? ChineseDescription { get; set; }
+    public int?    GroupId            { get; set; }
+    public int?    SubCategoryId      { get; set; }
+    /// <summary>Bilingual label of the suggested group, e.g. "Consumables / 消耗品".</summary>
+    public string? GroupLabel         { get; set; }
+    /// <summary>Bilingual label of the suggested sub-category, e.g. "Batteries / 電池".</summary>
+    public string? SubLabel           { get; set; }
+    /// <summary>Model self-reported confidence in the classification, 0..1.</summary>
+    public double  Confidence         { get; set; }
+}
+
+/// <summary>
+/// Request body for the expense-category AI assist endpoint: refine the name, translate to English,
+/// and suggest a Form 990 line for an expense category (大項/小項) being defined or edited.
+/// </summary>
+public class ExpenseCategoryAiRequest
+{
+    /// <summary>The user-typed Chinese name (the primary input).</summary>
+    public string  Name_zh             { get; set; } = "";
+    /// <summary>The English name, if already typed (extra context for the model).</summary>
+    public string? Name_en             { get; set; }
+    /// <summary>"group" (大項) or "sub" (小項); selects the prompt framing.</summary>
+    public string  Level               { get; set; } = "group";
+    /// <summary>For a sub-category: the parent group's bilingual name, used for context.</summary>
+    public string? ParentGroupName     { get; set; }
+    /// <summary>For a sub-category: the parent group's mapped Form 990 line id, used to bias the choice.</summary>
+    public int?    ParentForm990LineId { get; set; }
+}
+
+/// <summary>
+/// AI suggestion for an expense category: a refined Chinese name, an English translation, and a
+/// proposed Form 990 line. Line fields are null when the model returned an id outside the live catalog.
+/// </summary>
+public class CategoryAiSuggestion
+{
+    /// <summary>Typo-corrected, refined Traditional Chinese name.</summary>
+    public string? ChineseName      { get; set; }
+    public string? EnglishName      { get; set; }
+    public int?    Form990LineId    { get; set; }
+    /// <summary>Bilingual label of the suggested line, e.g. "16 — Occupancy / 場地".</summary>
+    public string? Form990LineLabel { get; set; }
+    /// <summary>Model self-reported confidence in the mapping, 0..1.</summary>
+    public double  Confidence       { get; set; }
+}

API/ROLAC.API/DTOs/Expense/ExpenseCategoryDtos.cs

@@ -11,6 +11,8 @@ public class ExpenseSubCategoryDto
     public bool    IsActive  { get; set; }
     public int?    Form990LineId   { get; set; }
     public string? Form990LineCode { get; set; }
+    public int?    Form1099BoxId   { get; set; }
+    public string? Form1099BoxCode { get; set; }
 }
 
 public class ExpenseCategoryGroupDto
@@ -22,6 +24,8 @@ public class ExpenseCategoryGroupDto
     public bool    IsActive  { get; set; }
     public int?    Form990LineId   { get; set; }
     public string? Form990LineCode { get; set; }
+    public int?    Form1099BoxId   { get; set; }
+    public string? Form1099BoxCode { get; set; }
     public List<ExpenseSubCategoryDto> SubCategories { get; set; } = [];
 }
 
@@ -31,6 +35,7 @@ public class CreateExpenseGroupRequest
     [MaxLength(200)] public string? Name_zh { get; set; }
     public int SortOrder { get; set; }
     public int? Form990LineId { get; set; }
+    public int? Form1099BoxId { get; set; }
 }
 public class UpdateExpenseGroupRequest : CreateExpenseGroupRequest
 {
@@ -44,6 +49,7 @@ public class CreateExpenseSubCategoryRequest
     [MaxLength(200)] public string? Name_zh { get; set; }
     public int SortOrder { get; set; }
     public int? Form990LineId { get; set; }
+    public int? Form1099BoxId { get; set; }
 }
 public class UpdateExpenseSubCategoryRequest : CreateExpenseSubCategoryRequest
 {

API/ROLAC.API/DTOs/Expense/ExpenseDtos.cs

@@ -1,52 +1,73 @@
 using System.ComponentModel.DataAnnotations;
 namespace ROLAC.API.DTOs.Expense;
 
+public class ExpenseLineItemDto
+{
+    public int      Id              { get; set; }
+    public int      CategoryGroupId { get; set; }
+    public string   CategoryGroupName { get; set; } = "";
+    public int      SubCategoryId   { get; set; }
+    public string   SubCategoryName { get; set; } = "";
+    public string?  FunctionalClass { get; set; }
+    public decimal  Amount          { get; set; }
+    public string?  Description     { get; set; }
+}
+
 public class ExpenseListItemDto
 {
     public int      Id          { get; set; }
     public string   Type        { get; set; } = "";
     public string   Status      { get; set; } = "";
-    public decimal  Amount      { get; set; }
+    public decimal  Amount      { get; set; }   // header total = sum of line amounts
     public string   Description { get; set; } = "";
     public int      MinistryId  { get; set; }
     public string   MinistryName { get; set; } = "";
-    public int      CategoryGroupId { get; set; }
+    public int      LineCount   { get; set; }
-    public string   CategoryGroupName { get; set; } = "";
+    public string   PrimaryCategoryName { get; set; } = "";   // first line's category (list hint; full breakdown via detail)
-    public int      SubCategoryId { get; set; }
-    public string   SubCategoryName { get; set; } = "";
     public string?  VendorName  { get; set; }
     public int?     MemberId    { get; set; }
-    public string?  MemberName  { get; set; }
+    public string?  MemberName  { get; set; }      // legal name "FirstName_en LastName_en" (used on the printed check)
+    public string?  MemberNickName { get; set; }   // "NickName LastName_en"; null when the member has no distinct nickname
     public string   ExpenseDate { get; set; } = "";   // yyyy-MM-dd
     public bool     HasReceipt  { get; set; }
     public string?  CheckNumber { get; set; }
-    public string?  FunctionalClass { get; set; }
+    // Review outcome — surfaced on the list so the Status column can show "Approved/Rejected by X · date".
+    public string?  ReviewedByName { get; set; }       // resolved Member full name, email fallback
+    public DateTimeOffset? ReviewedAt { get; set; }
+    public string?  ReviewNotes { get; set; }          // reject reason (or approval note)
+    public int?     PayeeId     { get; set; }
 }
 
 public class ExpenseDto : ExpenseListItemDto
 {
     public string?  Notes       { get; set; }
-    public string?  ReviewNotes { get; set; }
     public string?  SubmittedBy { get; set; }
     public DateTimeOffset? SubmittedAt { get; set; }
-    public DateTimeOffset? ReviewedAt  { get; set; }
     public DateTimeOffset? PaidAt      { get; set; }
+    public List<ExpenseLineItemDto> Lines { get; set; } = new();
+}
+
+public class ExpenseLineInput
+{
+    [Required] public int    CategoryGroupId { get; set; }
+    [Required] public int    SubCategoryId   { get; set; }
+    [Range(0.01, 9_999_999)] public decimal Amount { get; set; }
+    [MaxLength(20)]  public string? FunctionalClass { get; set; }
+    [MaxLength(500)] public string? Description { get; set; }
 }
 
 public class CreateExpenseRequest
 {
     [Required] public string Type { get; set; } = "StaffReimbursement"; // VendorPayment|StaffReimbursement
     [Required] public int    MinistryId      { get; set; }
-    [Required] public int    CategoryGroupId { get; set; }
+    [Required, MinLength(1)] public List<ExpenseLineInput> Lines { get; set; } = new();
-    [Required] public int    SubCategoryId   { get; set; }
-    [Range(0.01, 9_999_999)] public decimal Amount { get; set; }
     [Required, MaxLength(500)] public string Description { get; set; } = "";
     [MaxLength(200)] public string? VendorName { get; set; }
     public int?     MemberId    { get; set; }   // ignored for self-service (server uses caller)
     [MaxLength(50)] public string? CheckNumber { get; set; }
     [Required] public DateOnly ExpenseDate { get; set; }
     public string?  Notes { get; set; }
-    [MaxLength(20)] public string? FunctionalClass { get; set; }
+    public int?     PayeeId { get; set; }
 }
 public class UpdateExpenseRequest : CreateExpenseRequest { }
 

API/ROLAC.API/DTOs/Expense/ExpenseSnapshotDtos.cs

@@ -0,0 +1,42 @@
+using System.ComponentModel.DataAnnotations;
+namespace ROLAC.API.DTOs.Expense;
+
+public class ExpenseSnapshotLineDto
+{
+    public int      CategoryGroupId   { get; set; }
+    public string   CategoryGroupName { get; set; } = "";
+    public int      SubCategoryId     { get; set; }
+    public string   SubCategoryName   { get; set; } = "";
+    public string?  FunctionalClass   { get; set; }
+    public decimal  Amount            { get; set; }
+    public string?  Description       { get; set; }
+}
+
+public class ExpenseSnapshotDto
+{
+    public int      Id           { get; set; }
+    public string   Name         { get; set; } = "";
+    public int      MinistryId   { get; set; }
+    public string   MinistryName { get; set; } = "";
+    public string   Description  { get; set; } = "";
+    public string?  VendorName   { get; set; }
+    public string?  CheckNumber  { get; set; }
+    public string?  Notes        { get; set; }
+    public decimal  TotalAmount  { get; set; }   // sum of line amounts (list hint)
+    public int      LineCount    { get; set; }
+    public string?  CreatedByName { get; set; }  // resolved Member full name, email fallback
+    public DateTimeOffset CreatedAt { get; set; }
+    public List<ExpenseSnapshotLineDto> Lines { get; set; } = new();
+}
+
+public class CreateExpenseSnapshotRequest
+{
+    [Required, MaxLength(150)] public string Name { get; set; } = "";
+    [Required] public int MinistryId { get; set; }
+    [Required, MinLength(1)] public List<ExpenseLineInput> Lines { get; set; } = new();
+    [Required, MaxLength(500)] public string Description { get; set; } = "";
+    [MaxLength(200)] public string? VendorName  { get; set; }
+    [MaxLength(50)]  public string? CheckNumber { get; set; }
+    public string? Notes { get; set; }
+}
+public class UpdateExpenseSnapshotRequest : CreateExpenseSnapshotRequest { }

API/ROLAC.API/DTOs/Finance/Form1099ReportDtos.cs

@@ -0,0 +1,52 @@
+namespace ROLAC.API.DTOs.Finance;
+
+public class Form1099BoxDto
+{
+    public int    Id        { get; set; }
+    public string BoxCode   { get; set; } = "";
+    public string Name_en   { get; set; } = "";
+    public string? Name_zh  { get; set; }
+    public string FormType  { get; set; } = "";
+    public int    SortOrder { get; set; }
+}
+
+public class Form1099RecipientRowDto
+{
+    public int     PayeeId       { get; set; }
+    public string  LegalName     { get; set; } = "";
+    public string? TinLast4      { get; set; }
+    public string  W9Status      { get; set; } = "";
+    public decimal NecTotal      { get; set; }
+    public decimal RentsTotal    { get; set; }
+    public decimal GrandTotal    { get; set; }
+    public bool    MeetsThreshold { get; set; }
+    public bool    W9Missing     { get; set; }
+}
+
+public class Form1099SummaryDto
+{
+    public int TaxYear { get; set; }
+    public List<Form1099RecipientRowDto> Rows { get; set; } = [];
+    public decimal TotalReportable        { get; set; }
+    public int     RecipientsAtThreshold  { get; set; }
+    public int     RecipientsMissingW9    { get; set; }
+}
+
+public class Form1099PaymentDto
+{
+    public string  PaidDate     { get; set; } = "";
+    public string  Description  { get; set; } = "";
+    public string  CategoryName { get; set; } = "";
+    public string  BoxCode      { get; set; } = "";
+    public decimal Amount       { get; set; }
+}
+
+public class Form1099RecipientDetailDto
+{
+    public int    PayeeId   { get; set; }
+    public string LegalName { get; set; } = "";
+    public string? TinLast4 { get; set; }
+    public string W9Status  { get; set; } = "";
+    public int    TaxYear   { get; set; }
+    public List<Form1099PaymentDto> Payments { get; set; } = [];
+}

API/ROLAC.API/DTOs/Payee/Payee1099Dtos.cs

@@ -0,0 +1,54 @@
+using System.ComponentModel.DataAnnotations;
+namespace ROLAC.API.DTOs.Payee;
+
+public class Payee1099ListItemDto
+{
+    public int     Id                { get; set; }
+    public string  LegalName         { get; set; } = "";
+    public string? DisplayName       { get; set; }
+    public int?    MemberId          { get; set; }
+    public string? MemberName        { get; set; }
+    public string  TaxClassification { get; set; } = "";
+    public bool    Is1099Tracked     { get; set; }
+    public string? TinType           { get; set; }
+    public string? TinLast4          { get; set; }
+    public string  W9Status          { get; set; } = "";
+    public bool    IsActive          { get; set; }
+}
+
+public class Payee1099Dto : Payee1099ListItemDto
+{
+    public string? AddressLine1 { get; set; }
+    public string? AddressLine2 { get; set; }
+    public string? City  { get; set; }
+    public string? State { get; set; }
+    public string? Zip   { get; set; }
+    public string? Email { get; set; }
+    public string? Phone { get; set; }
+    public string? W9ReceivedDate { get; set; }
+    public bool    HasW9Document  { get; set; }
+    public string? Notes { get; set; }
+}
+
+public class SavePayee1099Request
+{
+    [Required, MaxLength(200)] public string LegalName { get; set; } = "";
+    [MaxLength(200)] public string? DisplayName { get; set; }
+    public int? MemberId { get; set; }
+    [Required, MaxLength(40)] public string TaxClassification { get; set; } = "Individual";
+    public bool Is1099Tracked { get; set; } = true;
+    [MaxLength(10)] public string? TinType { get; set; }
+    /// <summary>Plain TIN; null = leave unchanged on update. Encrypted server-side.</summary>
+    public string? Tin { get; set; }
+    [MaxLength(100)] public string? AddressLine1 { get; set; }
+    [MaxLength(100)] public string? AddressLine2 { get; set; }
+    [MaxLength(60)]  public string? City  { get; set; }
+    [MaxLength(2)]   public string? State { get; set; }
+    [MaxLength(10)]  public string? Zip   { get; set; }
+    [MaxLength(120)] public string? Email { get; set; }
+    [MaxLength(40)]  public string? Phone { get; set; }
+    [MaxLength(20)]  public string  W9Status { get; set; } = "Missing";
+    public DateOnly? W9ReceivedDate { get; set; }
+    public bool      IsActive { get; set; } = true;
+    public string?   Notes { get; set; }
+}

API/ROLAC.API/Data/AppDbContext.cs

@@ -21,7 +21,12 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
     public DbSet<ExpenseCategoryGroup> ExpenseCategoryGroups => Set<ExpenseCategoryGroup>();
     public DbSet<ExpenseSubCategory>   ExpenseSubCategories  => Set<ExpenseSubCategory>();
     public DbSet<Form990ExpenseLine> Form990ExpenseLines => Set<Form990ExpenseLine>();
+    public DbSet<Payee1099>          Payee1099s           => Set<Payee1099>();
+    public DbSet<Form1099Box>        Form1099Boxes        => Set<Form1099Box>();
     public DbSet<Expense>          Expenses          => Set<Expense>();
+    public DbSet<ExpenseLine>      ExpenseLines      => Set<ExpenseLine>();
+    public DbSet<ExpenseSnapshot>     ExpenseSnapshots     => Set<ExpenseSnapshot>();
+    public DbSet<ExpenseSnapshotLine> ExpenseSnapshotLines => Set<ExpenseSnapshotLine>();
     public DbSet<MonthlyStatement> MonthlyStatements => Set<MonthlyStatement>();
     public DbSet<ChurchProfile>    ChurchProfiles    => Set<ChurchProfile>();
     public DbSet<Check>            Checks            => Set<Check>();
@@ -215,6 +220,45 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
             entity.HasIndex(e => e.LineCode).IsUnique();
         });
 
+        // ── Form1099Box (1099 reporting box catalog) ──────────────────────────
+        builder.Entity<Form1099Box>(entity =>
+        {
+            entity.Property(e => e.BoxCode).HasMaxLength(10).IsRequired();
+            entity.Property(e => e.Name_en).HasMaxLength(200).IsRequired();
+            entity.Property(e => e.Name_zh).HasMaxLength(200);
+            entity.Property(e => e.FormType).HasMaxLength(20).IsRequired();
+            entity.Property(e => e.CreatedBy).HasMaxLength(450);
+            entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+            entity.HasIndex(e => e.BoxCode).IsUnique();
+        });
+
+        // ── Payee1099 (1099 recipient master) ────────────────────────────────
+        builder.Entity<Payee1099>(entity =>
+        {
+            entity.HasQueryFilter(p => !p.IsDeleted);
+            entity.Property(e => e.LegalName).HasMaxLength(200).IsRequired();
+            entity.Property(e => e.DisplayName).HasMaxLength(200);
+            entity.Property(e => e.TaxClassification).HasMaxLength(40).IsRequired();
+            entity.Property(e => e.TinType).HasMaxLength(10);
+            entity.Property(e => e.TinLast4).HasMaxLength(4);
+            entity.Property(e => e.State).HasMaxLength(2);
+            entity.Property(e => e.Zip).HasMaxLength(10);
+            entity.Property(e => e.W9Status).HasMaxLength(20).HasDefaultValue(Form1099.W9Status.Missing);
+            entity.Property(e => e.AddressLine1).HasMaxLength(200);
+            entity.Property(e => e.AddressLine2).HasMaxLength(200);
+            entity.Property(e => e.City).HasMaxLength(100);
+            entity.Property(e => e.Email).HasMaxLength(200);
+            entity.Property(e => e.Phone).HasMaxLength(30);
+            entity.Property(e => e.Notes).HasMaxLength(500);
+            entity.Property(e => e.W9BlobPath).HasMaxLength(500);
+            entity.Property(e => e.TinEncrypted).HasMaxLength(500);
+            entity.Property(e => e.CreatedBy).HasMaxLength(450);
+            entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+            entity.Property(e => e.DeletedBy).HasMaxLength(450);
+            entity.HasOne(e => e.Member).WithMany()
+                  .HasForeignKey(e => e.MemberId).OnDelete(DeleteBehavior.SetNull);
+        });
+
         // ── ExpenseCategoryGroup ─────────────────────────────────────────────
         builder.Entity<ExpenseCategoryGroup>(entity =>
         {
@@ -224,6 +268,8 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
             entity.Property(e => e.UpdatedBy).HasMaxLength(450);
             entity.HasOne(e => e.Form990Line).WithMany()
                   .HasForeignKey(e => e.Form990LineId).OnDelete(DeleteBehavior.SetNull);
+            entity.HasOne(e => e.Form1099Box).WithMany()
+                  .HasForeignKey(e => e.Form1099BoxId).OnDelete(DeleteBehavior.SetNull);
         });
 
         // ── ExpenseSubCategory ───────────────────────────────────────────────
@@ -237,6 +283,8 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
                   .HasForeignKey(e => e.GroupId).OnDelete(DeleteBehavior.Restrict);
             entity.HasOne(e => e.Form990Line).WithMany()
                   .HasForeignKey(e => e.Form990LineId).OnDelete(DeleteBehavior.SetNull);
+            entity.HasOne(e => e.Form1099Box).WithMany()
+                  .HasForeignKey(e => e.Form1099BoxId).OnDelete(DeleteBehavior.SetNull);
         });
 
         // ── Expense ──────────────────────────────────────────────────────────
@@ -246,7 +294,6 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
 
             entity.Property(e => e.Type).HasMaxLength(30).IsRequired();
             entity.Property(e => e.Status).HasMaxLength(30).HasDefaultValue("Draft");
-            entity.Property(e => e.FunctionalClass).HasMaxLength(20);
             entity.Property(e => e.Amount).HasColumnType("decimal(18,2)");
             entity.Property(e => e.Description).HasMaxLength(500).IsRequired();
             entity.Property(e => e.VendorName).HasMaxLength(200);
@@ -266,12 +313,73 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
 
             entity.HasOne(e => e.Ministry).WithMany()
                   .HasForeignKey(e => e.MinistryId).OnDelete(DeleteBehavior.Restrict);
+            entity.HasOne(e => e.Member).WithMany()
+                  .HasForeignKey(e => e.MemberId).OnDelete(DeleteBehavior.SetNull);
+            entity.HasOne(e => e.Payee).WithMany()
+                  .HasForeignKey(e => e.PayeeId).OnDelete(DeleteBehavior.SetNull);
+        });
+
+        // ── ExpenseLine (category breakdown of one Expense) ──────────────────
+        builder.Entity<ExpenseLine>(entity =>
+        {
+            // Mirror the parent Expense's soft-delete filter (required relationship).
+            entity.HasQueryFilter(l => !l.Expense!.IsDeleted);
+
+            entity.Property(e => e.FunctionalClass).HasMaxLength(20);
+            entity.Property(e => e.Amount).HasColumnType("decimal(18,2)");
+            entity.Property(e => e.Description).HasMaxLength(500);
+            entity.Property(e => e.CreatedBy).HasMaxLength(450);
+            entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+
+            entity.HasIndex(e => e.ExpenseId);
+
+            entity.HasOne(e => e.Expense).WithMany(x => x.Lines)
+                  .HasForeignKey(e => e.ExpenseId).OnDelete(DeleteBehavior.Cascade);
+            entity.HasOne(e => e.CategoryGroup).WithMany()
+                  .HasForeignKey(e => e.CategoryGroupId).OnDelete(DeleteBehavior.Restrict);
+            entity.HasOne(e => e.SubCategory).WithMany()
+                  .HasForeignKey(e => e.SubCategoryId).OnDelete(DeleteBehavior.Restrict);
+        });
+
+        // ── ExpenseSnapshot (reusable vendor-payment template) ───────────────
+        builder.Entity<ExpenseSnapshot>(entity =>
+        {
+            entity.HasQueryFilter(s => !s.IsDeleted);
+
+            entity.Property(e => e.Name).HasMaxLength(150).IsRequired();
+            entity.Property(e => e.Description).HasMaxLength(500).IsRequired();
+            entity.Property(e => e.VendorName).HasMaxLength(200);
+            entity.Property(e => e.CheckNumber).HasMaxLength(50);
+            entity.Property(e => e.CreatedBy).HasMaxLength(450);
+            entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+            entity.Property(e => e.DeletedBy).HasMaxLength(450);
+
+            entity.HasIndex(e => e.CreatedAt);
+
+            entity.HasOne(e => e.Ministry).WithMany()
+                  .HasForeignKey(e => e.MinistryId).OnDelete(DeleteBehavior.Restrict);
+        });
+
+        // ── ExpenseSnapshotLine (category breakdown of one snapshot) ─────────
+        builder.Entity<ExpenseSnapshotLine>(entity =>
+        {
+            // Mirror the parent snapshot's soft-delete filter (required relationship).
+            entity.HasQueryFilter(l => !l.Snapshot!.IsDeleted);
+
+            entity.Property(e => e.FunctionalClass).HasMaxLength(20);
+            entity.Property(e => e.Amount).HasColumnType("decimal(18,2)");
+            entity.Property(e => e.Description).HasMaxLength(500);
+            entity.Property(e => e.CreatedBy).HasMaxLength(450);
+            entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+
+            entity.HasIndex(e => e.SnapshotId);
+
+            entity.HasOne(e => e.Snapshot).WithMany(x => x.Lines)
+                  .HasForeignKey(e => e.SnapshotId).OnDelete(DeleteBehavior.Cascade);
             entity.HasOne(e => e.CategoryGroup).WithMany()
                   .HasForeignKey(e => e.CategoryGroupId).OnDelete(DeleteBehavior.Restrict);
             entity.HasOne(e => e.SubCategory).WithMany()
                   .HasForeignKey(e => e.SubCategoryId).OnDelete(DeleteBehavior.Restrict);
-            entity.HasOne(e => e.Member).WithMany()
-                  .HasForeignKey(e => e.MemberId).OnDelete(DeleteBehavior.SetNull);
         });
 
         // ── ChurchProfile (singleton settings) ───────────────────────────────
@@ -285,12 +393,18 @@ public class AppDbContext : IdentityDbContext<AppUser, AppRole, string>
             entity.Property(e => e.BankName).HasMaxLength(200);
             entity.Property(e => e.BankAccountNumber).HasMaxLength(50);
             entity.Property(e => e.BankRoutingNumber).HasMaxLength(50);
+            entity.Property(e => e.PayerEin).HasMaxLength(20);
             entity.Property(e => e.NameZh).HasMaxLength(200);
             entity.Property(e => e.Phone).HasMaxLength(50);
             entity.Property(e => e.Email).HasMaxLength(200);
             entity.Property(e => e.Website).HasMaxLength(300);
             entity.Property(e => e.CreatedBy).HasMaxLength(450);
             entity.Property(e => e.UpdatedBy).HasMaxLength(450);
+            entity.Property(e => e.AiProvider).HasMaxLength(20).HasDefaultValue("Claude");
+            entity.Property(e => e.ClaudeModel).HasMaxLength(100).HasDefaultValue("claude-haiku-4-5-20251001");
+            entity.Property(e => e.ClaudeApiKey).HasMaxLength(500);
+            entity.Property(e => e.GeminiModel).HasMaxLength(100).HasDefaultValue("gemini-2.5-flash-lite");
+            entity.Property(e => e.GeminiApiKey).HasMaxLength(500);
             // Optimistic-concurrency token for safe check-number allocation.
             entity.Property(e => e.xmin).IsRowVersion();
         });

API/ROLAC.API/Data/DbSeeder.cs

@@ -28,6 +28,8 @@ public static class DbSeeder
         ("Hospitality",    "招待",     8),
         ("Children",       "兒牧",     9),
         ("Catering",       "餐飲",    10),
+        ("Cell Groups",    "小組牧養", 11),
+        ("Special Events", "特別活動", 12),
     ];
 
     // (GroupEn, GroupZh, Sort, SubItems[(SubEn, SubZh)])
@@ -38,11 +40,11 @@ public static class DbSeeder
         ("Food & Beverage", "餐飲", 3, [("Catering","出餐費用"),("Food Ingredients","食材採購"),("Utensils","器具"),("Disposable Tableware","一次性餐具")]),
         ("Training", "培訓", 4, [("Course Fees","課程費用"),("Books","書籍"),("Conference","研討會"),("Travel","差旅")]),
         ("Materials", "教材", 5, [("Curriculum Printing","教材印刷"),("Craft Supplies","手工材料"),("Copyright & Licensing","版權購買")]),
-        ("Facility", "場地", 6, [("Rent","場地租金"),("Utilities","水電"),("Property Insurance","財產保險"),("Decoration","裝飾")]),
+        ("Facility", "場地", 6, [("Rent","場地租金"),("Utilities","水電"),("Property Insurance","財產保險"),("Decoration","裝飾"),("Repairs & Maintenance","修繕維護")]),
         ("Printing", "印刷", 7, [("Bulletins","週報"),("Order of Service","程序單"),("Posters","海報"),("Advertising & Promotion","廣告推廣")]),
         ("Missions", "宣教", 8, [("Offering Transfer","奉獻轉帳"),("Missionary Support","宣教士支援"),("Foreign Missions Support","國外宣教支援"),("Travel","差旅")]),
         ("Benevolence", "關懷救助", 9, [("Emergency Aid","急難救助"),("Condolence Gifts","慰問禮品"),("Visit Expenses","探訪費用")]),
-        ("Other", "其他", 10, [("Miscellaneous","雜支")]),
+        ("Other", "其他", 10, [("Miscellaneous","雜支"),("Gifts","禮品")]),
         ("Personnel", "人事", 11, [("Officer / Key Employee Compensation","主要職員薪酬"),("Salary & Wages","薪資"),("Payroll Taxes","薪資稅費"),("Employee Benefits","員工福利"),("Retirement / Pension","退休金"),("Workers Compensation","勞工保險"),("Honorarium","酬庸"),("Staff Training","同工進修"),("Contract Labor","外包勞務")]),
         ("Professional Services", "專業服務", 12, [("Legal","法律服務"),("Accounting & Audit","會計與審計"),("Other Professional","其他專業服務")]),
         ("Information Technology", "資訊科技", 13, [("Software & Subscriptions","軟體與訂閱"),("Website & Hosting","網站與主機"),("Internet & Telecom","網路與電信")]),
@@ -91,23 +93,36 @@ public static class DbSeeder
         ("Facility",  "Utilities",           "16"),
         ("Facility",  "Property Insurance",  "23"),
         ("Facility",  "Decoration",          "24"),
+        // Building repairs & maintenance (plumbing, electrical, painting) are part of Occupancy.
+        ("Facility",  "Repairs & Maintenance", "16"),
         ("Training",  "Course Fees",         "19"),
         ("Training",  "Conference",          "19"),
         ("Training",  "Books",               "24"),
         ("Training",  "Travel",              "17"),
         ("Missions",  "Travel",              "17"),
-        ("Missions",  "Offering Transfer",   "1"),
+        // Domestic missions support is paid to individual missionaries/families → line 2 (grants to individuals).
-        ("Missions",  "Missionary Support",  "1"),
+        ("Missions",  "Offering Transfer",   "2"),
+        ("Missions",  "Missionary Support",  "2"),
         ("Missions",  "Foreign Missions Support", "3"),
         ("Benevolence", "Emergency Aid",     "2"),
         ("Benevolence", "Condolence Gifts",  "2"),
-        ("Benevolence", "Visit Expenses",    "2"),
+        // Visitation is the church's own travel/program cost, not a grant to an individual.
+        ("Benevolence", "Visit Expenses",    "17"),
         ("Consumables", "Office Supplies",   "13"),
+        // General supplies belong with office expenses (line 13), not the "Other" catch-all.
+        ("Consumables", "Batteries",         "13"),
+        ("Consumables", "Accessories",       "13"),
+        ("Consumables", "Cleaning Supplies", "13"),
+        // IRS line 13 covers equipment rental and maintenance.
+        ("Equipment",   "Rental",                "13"),
+        ("Equipment",   "Maintenance & Repair",  "13"),
         ("Printing",  "Bulletins",           "13"),
         ("Printing",  "Order of Service",    "13"),
         ("Printing",  "Posters",             "12"),
         ("Printing",  "Advertising & Promotion", "12"),
         ("Materials", "Curriculum Printing", "13"),
+        // Classroom/craft supplies fall under IRS line 13 office expenses ("supplies… classroom…").
+        ("Materials", "Craft Supplies",      "13"),
         ("Professional Services", "Legal",   "11b"),
         ("Professional Services", "Accounting & Audit", "11c"),
         ("Professional Services", "Other Professional", "11g"),
@@ -115,6 +130,39 @@ public static class DbSeeder
         ("Information Technology", "Website & Hosting", "14"),
         ("Information Technology", "Internet & Telecom", "14"),
         ("Finance & Banking", "Interest",    "20"),
+        // Bank/processing fees are office expenses per IRS line 13 (consistent with Interest → 20).
+        ("Finance & Banking", "Bank & Processing Fees", "13"),
+        // Appreciation/outreach gifts have no natural 990 line; mapped to 24 explicitly so this
+        // deliberate "Other" choice doesn't inflate UnmappedExpenseCount. (Benevolence gifts → line 2.)
+        ("Other", "Gifts", "24"),
+    ];
+
+    private static readonly (string Code, string En, string Zh, string FormType, int Sort)[] Form1099BoxSeed =
+    [
+        (Form1099.BoxNec1,  "Nonemployee compensation", "非員工報酬", "1099-NEC",  1),
+        (Form1099.BoxMisc1, "Rents",                    "租金",       "1099-MISC", 2),
+    ];
+
+    // Only service/rent subcategories get a box. Everything else stays unmapped (not reportable).
+    private static readonly (string GroupEn, string SubEn, string Code)[] Form1099SubMappingSeed =
+    [
+        ("Personnel",             "Honorarium",          Form1099.BoxNec1),
+        ("Personnel",             "Contract Labor",      Form1099.BoxNec1),
+        ("Professional Services", "Legal",               Form1099.BoxNec1),
+        ("Professional Services", "Accounting & Audit",  Form1099.BoxNec1),
+        ("Professional Services", "Other Professional",  Form1099.BoxNec1),
+        ("Facility",              "Rent",                Form1099.BoxMisc1),
+    ];
+
+    // One-time corrections for subcategories that were mapped to the WRONG line in an earlier
+    // seed. The normal mapping loop below only fills NULLs, so it cannot fix an existing bad
+    // value — this block does. Idempotent: each row fires only while the subcategory still holds
+    // the OLD line, so it never clobbers a deliberate admin re-mapping. (GroupEn, SubEn, Old, New)
+    private static readonly (string GroupEn, string SubEn, string OldCode, string NewCode)[] Form990RemapSeed =
+    [
+        ("Benevolence", "Visit Expenses",     "2", "17"),
+        ("Missions",    "Missionary Support", "1", "2"),
+        ("Missions",    "Offering Transfer",  "1", "2"),
     ];
 
     private static readonly (string Name, string Description)[] Roles =
@@ -159,6 +207,11 @@ public static class DbSeeder
         ("finance", Modules.ChurchProfile,     true, true,  false, false),
         ("finance", Modules.Disbursements,     true, true,  true,  true),
         ("finance", Modules.Form990Report,     true, false, false, false),
+        // Form1099 — finance manages recipients and tracks filings; pastor and board_member
+        // get read-only oversight (same pattern as Form990Report). No Approve semantics.
+        ("finance",      Modules.Form1099, true, true,  true,  false),
+        ("pastor",       Modules.Form1099, true, false, false, false),
+        ("board_member", Modules.Form1099, true, false, false, false),
 
         // Logs — read-only. System logs are technical (pastor only); audit logs have
         // governance value, so finance and board members can read them too.
@@ -329,6 +382,37 @@ public static class DbSeeder
             if (sub is not null && sub.Form990LineId is null && linesByCode.TryGetValue(code, out var lineId))
                 sub.Form990LineId = lineId;
         }
+
+        // Correct earlier mis-mappings on existing databases (see Form990RemapSeed). Only fires
+        // while the subcategory still holds the OLD line, so a later admin edit is never clobbered.
+        foreach (var (groupEn, subEn, oldCode, newCode) in Form990RemapSeed)
+        {
+            var sub = subsByKey.FirstOrDefault(s => s.Group!.Name_en == groupEn && s.Name_en == subEn);
+            if (sub is null) continue;
+            if (linesByCode.TryGetValue(oldCode, out var oldId)
+                && linesByCode.TryGetValue(newCode, out var newId)
+                && sub.Form990LineId == oldId)
+                sub.Form990LineId = newId;
+        }
+        await db.SaveChangesAsync();
+    }
+
+    public static async Task SeedForm1099BoxesAsync(AppDbContext db)
+    {
+        foreach (var (code, en, zh, formType, sort) in Form1099BoxSeed)
+            if (!await db.Form1099Boxes.AnyAsync(b => b.BoxCode == code))
+                db.Form1099Boxes.Add(new Form1099Box
+                    { BoxCode = code, Name_en = en, Name_zh = zh, FormType = formType, SortOrder = sort, IsActive = true });
+        await db.SaveChangesAsync();
+
+        var boxesByCode = await db.Form1099Boxes.ToDictionaryAsync(b => b.BoxCode, b => b.Id);
+        var subs = await db.ExpenseSubCategories.Include(s => s.Group).ToListAsync();
+        foreach (var (groupEn, subEn, code) in Form1099SubMappingSeed)
+        {
+            var sub = subs.FirstOrDefault(s => s.Group!.Name_en == groupEn && s.Name_en == subEn);
+            if (sub is not null && sub.Form1099BoxId is null && boxesByCode.TryGetValue(code, out var boxId))
+                sub.Form1099BoxId = boxId;
+        }
         await db.SaveChangesAsync();
     }
 
@@ -411,6 +495,7 @@ public static class DbSeeder
         await SeedMinistriesAsync(db);
         await SeedExpenseCategoriesAsync(db);
         await SeedForm990ExpenseLinesAsync(db);
+        await SeedForm1099BoxesAsync(db);
         await SeedChurchProfileAsync(db);
         await SeedSiteSettingAsync(db);
         await SeedNotificationSettingAsync(db, config);

API/ROLAC.API/Data/MockFinanceData.sql

@@ -157,6 +157,8 @@ rows AS (
     mi."Id"  AS ministry_id,
     gp."Id"  AS group_id,
     sc."Id"  AS sub_id,
+    -- pre-allocate the expense id so the matching ExpenseLine can reference it
+    nextval(pg_get_serial_sequence('"Expenses"','Id')) AS new_id,
     sp.is_reimb,
     sp.vendor,
     sp.descr,
@@ -172,13 +174,14 @@ rows AS (
   JOIN "ExpenseCategoryGroups" gp ON gp."Name_en" = sp.grp
   JOIN "ExpenseSubCategories"  sc ON sc."Name_en" = sp.sub AND sc."GroupId" = gp."Id"
 )
+, ins_exp AS (
 INSERT INTO "Expenses"
-  ("MinistryId","CategoryGroupId","SubCategoryId","Type","Status","Amount",
+  ("Id","MinistryId","Type","Status","Amount",
    "Description","VendorName","MemberId","CheckNumber","ExpenseDate",
    "Notes","SubmittedBy","SubmittedAt","ReviewedBy","ReviewedAt","PaidBy","PaidAt",
    "CreatedAt","CreatedBy","UpdatedAt","UpdatedBy","IsDeleted")
 SELECT
-  r.ministry_id, r.group_id, r.sub_id,
+  r.new_id, r.ministry_id,
   CASE WHEN r.is_reimb THEN 'StaffReimbursement' ELSE 'VendorPayment' END,
   r.status,
   r.amount,
@@ -196,6 +199,15 @@ SELECT
   CASE WHEN r.status = 'Paid' THEN 'mockdata' END,
   CASE WHEN r.status = 'Paid' THEN r.expense_date::timestamptz END,
   r.expense_date::timestamptz, 'mockdata', r.expense_date::timestamptz, 'mockdata', false
+FROM rows r
+)
+-- one line per mock expense (single-category), mirroring the migrated production shape
+INSERT INTO "ExpenseLines"
+  ("ExpenseId","CategoryGroupId","SubCategoryId","FunctionalClass","Amount","Description",
+   "CreatedAt","CreatedBy","UpdatedAt","UpdatedBy")
+SELECT
+  r.new_id, r.group_id, r.sub_id, NULL, r.amount, NULL,
+  r.expense_date::timestamptz, 'mockdata', r.expense_date::timestamptz, 'mockdata'
 FROM rows r;
 
 COMMIT;

API/ROLAC.API/Entities/ChurchProfile.cs

@@ -21,6 +21,16 @@ public class ChurchProfile : AuditableEntity, IAuditable
     public string? BankAccountNumber { get; set; }
     public string? BankRoutingNumber { get; set; }
 
+    /// <summary>Payer EIN printed on Form 1099-NEC Copy B; the church's own public business identifier.</summary>
+    public string? PayerEin          { get; set; }
+
+    // ── AI assist provider settings (editable via Church Profile → AI 設定 tab) ──
+    public string  AiProvider   { get; set; } = "Claude";   // "Claude" | "Gemini"
+    public string? ClaudeModel  { get; set; } = "claude-haiku-4-5-20251001";
+    public string? ClaudeApiKey { get; set; }                // secret, stored plaintext
+    public string? GeminiModel  { get; set; } = "gemini-2.5-flash-lite";
+    public string? GeminiApiKey { get; set; }                // secret, stored plaintext
+
     /// <summary>Next check number to allocate; consumed (++) when a check is issued.</summary>
     public int     NextCheckNumber   { get; set; } = 1001;
 

API/ROLAC.API/Entities/Expense.cs

@@ -5,15 +5,13 @@ public class Expense : SoftDeleteEntity, IAuditable
 {
     public int      Id              { get; set; }
     public int      MinistryId      { get; set; }
-    public int      CategoryGroupId { get; set; }
-    public int      SubCategoryId   { get; set; }
     public string   Type            { get; set; } = "StaffReimbursement"; // VendorPayment | StaffReimbursement
     public string   Status          { get; set; } = "Draft";             // see state machine
-    public string?  FunctionalClass { get; set; }   // null = inherit Ministry.DefaultFunctionalClass
+    public decimal  Amount          { get; set; }   // denormalized total = SUM(Lines.Amount), recomputed server-side
-    public decimal  Amount          { get; set; }
     public string   Description     { get; set; } = null!;
     public string?  VendorName      { get; set; }
     public int?     MemberId        { get; set; }
+    public int?     PayeeId         { get; set; }   // 1099 recipient attribution (header-level)
     public string?  CheckNumber     { get; set; }
     public DateOnly ExpenseDate     { get; set; }
     public string?  ReceiptBlobPath { get; set; }
@@ -27,7 +25,7 @@ public class Expense : SoftDeleteEntity, IAuditable
     public string?        PaidBy      { get; set; }
 
     public Ministry?         Ministry { get; set; }
-    public ExpenseCategoryGroup? CategoryGroup { get; set; }
-    public ExpenseSubCategory?   SubCategory   { get; set; }
     public Member?           Member   { get; set; }
+    public Payee1099?        Payee    { get; set; }
+    public List<ExpenseLine> Lines    { get; set; } = new();
 }

API/ROLAC.API/Entities/ExpenseCategoryGroup.cs

@@ -12,5 +12,8 @@ public class ExpenseCategoryGroup : AuditableEntity, IAuditable
     public int?                Form990LineId { get; set; }
     public Form990ExpenseLine? Form990Line   { get; set; }
 
+    public int?         Form1099BoxId { get; set; }   // null = not 1099-reportable
+    public Form1099Box? Form1099Box   { get; set; }
+
     public List<ExpenseSubCategory> SubCategories { get; set; } = [];
 }

API/ROLAC.API/Entities/ExpenseLine.cs

@@ -0,0 +1,23 @@
+using ROLAC.API.Entities.Base;
+namespace ROLAC.API.Entities;
+
+/// <summary>
+/// One category line of an <see cref="Expense"/>. A single invoice/payment can span
+/// multiple expense categories, so the category / amount / functional-class axis lives
+/// here per line; the Expense header keeps payment-level info and a denormalized total.
+/// Lines are wholly owned by the header (replaced as a set on update, like CheckLine).
+/// </summary>
+public class ExpenseLine : AuditableEntity
+{
+    public int      Id              { get; set; }
+    public int      ExpenseId       { get; set; }
+    public int      CategoryGroupId { get; set; }
+    public int      SubCategoryId   { get; set; }
+    public string?  FunctionalClass { get; set; }   // null = inherit Ministry.DefaultFunctionalClass
+    public decimal  Amount          { get; set; }
+    public string?  Description     { get; set; }    // optional per-line note (header description is authoritative for check printing)
+
+    public Expense?              Expense       { get; set; }
+    public ExpenseCategoryGroup? CategoryGroup { get; set; }
+    public ExpenseSubCategory?   SubCategory   { get; set; }
+}

API/ROLAC.API/Entities/ExpenseSnapshot.cs

@@ -0,0 +1,22 @@
+using ROLAC.API.Entities.Base;
+namespace ROLAC.API.Entities;
+
+/// <summary>
+/// A reusable template of a vendor payment. Lets finance save a recurring fixed expense
+/// (rent, internet, a fixed catered-meal cost) and re-apply it later, pre-filling everything
+/// except the ExpenseDate. Shared church-wide; the creator is the auditable CreatedBy.
+/// Lines are wholly owned by the header (replaced as a set on update, like ExpenseLine).
+/// </summary>
+public class ExpenseSnapshot : SoftDeleteEntity
+{
+    public int      Id          { get; set; }
+    public string   Name        { get; set; } = null!;   // user label, e.g. "Monthly Rent — Landlord X"
+    public int      MinistryId  { get; set; }
+    public string   Description { get; set; } = null!;
+    public string?  VendorName  { get; set; }
+    public string?  CheckNumber { get; set; }
+    public string?  Notes       { get; set; }
+
+    public Ministry?                 Ministry { get; set; }
+    public List<ExpenseSnapshotLine> Lines    { get; set; } = new();
+}

API/ROLAC.API/Entities/ExpenseSnapshotLine.cs

@@ -0,0 +1,18 @@
+using ROLAC.API.Entities.Base;
+namespace ROLAC.API.Entities;
+
+/// <summary>One category line of an <see cref="ExpenseSnapshot"/>, mirroring <see cref="ExpenseLine"/>.</summary>
+public class ExpenseSnapshotLine : AuditableEntity
+{
+    public int      Id              { get; set; }
+    public int      SnapshotId      { get; set; }
+    public int      CategoryGroupId { get; set; }
+    public int      SubCategoryId   { get; set; }
+    public string?  FunctionalClass { get; set; }   // null = inherit Ministry.DefaultFunctionalClass
+    public decimal  Amount          { get; set; }
+    public string?  Description     { get; set; }
+
+    public ExpenseSnapshot?      Snapshot      { get; set; }
+    public ExpenseCategoryGroup? CategoryGroup { get; set; }
+    public ExpenseSubCategory?   SubCategory   { get; set; }
+}

API/ROLAC.API/Entities/ExpenseSubCategory.cs

@@ -13,5 +13,8 @@ public class ExpenseSubCategory : AuditableEntity, IAuditable
     public int?                Form990LineId { get; set; }
     public Form990ExpenseLine? Form990Line   { get; set; }
 
+    public int?         Form1099BoxId { get; set; }   // null = not 1099-reportable
+    public Form1099Box? Form1099Box   { get; set; }
+
     public ExpenseCategoryGroup? Group { get; set; }
 }

API/ROLAC.API/Entities/Form1099.cs

@@ -0,0 +1,20 @@
+namespace ROLAC.API.Entities;
+
+/// <summary>Shared 1099 constants. Box codes match Form1099Box.BoxCode seed values.</summary>
+public static class Form1099
+{
+    /// <summary>IRS reporting threshold (USD) per box, per recipient, per calendar year.</summary>
+    public const decimal ReportingThreshold = 600m;
+
+    public const string BoxNec1  = "NEC-1";   // Nonemployee compensation
+    public const string BoxMisc1 = "MISC-1";  // Rents
+
+    public static class W9Status
+    {
+        public const string Missing   = "Missing";
+        public const string Requested = "Requested";
+        public const string OnFile    = "OnFile";
+        public const string Expired   = "Expired";
+        public static readonly IReadOnlyList<string> All = [Missing, Requested, OnFile, Expired];
+    }
+}

API/ROLAC.API/Entities/Form1099Box.cs

@@ -0,0 +1,14 @@
+using ROLAC.API.Entities.Base;
+namespace ROLAC.API.Entities;
+
+/// <summary>A 1099 reporting box, e.g. "NEC-1 — Nonemployee compensation".</summary>
+public class Form1099Box : AuditableEntity, IAuditable
+{
+    public int     Id        { get; set; }
+    public string  BoxCode   { get; set; } = null!;   // "NEC-1", "MISC-1"
+    public string  Name_en   { get; set; } = null!;
+    public string? Name_zh   { get; set; }
+    public string  FormType  { get; set; } = "1099-NEC";  // "1099-NEC" | "1099-MISC"
+    public int     SortOrder { get; set; }
+    public bool    IsActive  { get; set; } = true;
+}

API/ROLAC.API/Entities/FunctionalClasses.cs

@@ -2,7 +2,7 @@ namespace ROLAC.API.Entities;
 
 /// <summary>
 /// The three IRS Form 990 Part IX functional-expense columns. Stored verbatim in
-/// Ministry.DefaultFunctionalClass and Expense.FunctionalClass.
+/// Ministry.DefaultFunctionalClass and ExpenseLine.FunctionalClass.
 /// </summary>
 public static class FunctionalClasses
 {

API/ROLAC.API/Entities/Logging/AuditLog.cs

@@ -53,6 +53,7 @@ public static class AuditActions
     public const string CheckIssued        = "CheckIssued";
     public const string CheckVoided        = "CheckVoided";
     public const string ExpenseApproved    = "ExpenseApproved";
+    public const string ExpenseRejected    = "ExpenseRejected";
     public const string StatementFinalized = "StatementFinalized";
 
     public static readonly IReadOnlyList<string> All =
@@ -60,7 +61,7 @@ public static class AuditActions
         Create, Update, Delete, Login, Logout, LoginFailed, RoleChanged,
         PasswordChanged, UserDeactivated, PermissionChanged,
         InvitationCreated, InvitationAccepted, CheckIssued,
-        CheckVoided, ExpenseApproved, StatementFinalized,
+        CheckVoided, ExpenseApproved, ExpenseRejected, StatementFinalized,
     ];
 }
 

API/ROLAC.API/Entities/Payee1099.cs

@@ -0,0 +1,32 @@
+using ROLAC.API.Entities.Base;
+namespace ROLAC.API.Entities;
+
+/// <summary>
+/// A 1099 recipient (independent contractor / vendor). Holds W-9 data and an encrypted TIN.
+/// Optionally linked to a Member (e.g. a part-time co-worker paid as a contractor).
+/// </summary>
+public class Payee1099 : SoftDeleteEntity, IAuditable
+{
+    public int     Id                { get; set; }
+    public string  LegalName         { get; set; } = null!;     // name on the W-9
+    public string? DisplayName       { get; set; }              // friendly / DBA
+    public int?    MemberId          { get; set; }
+    public Member? Member            { get; set; }
+    public string  TaxClassification { get; set; } = "Individual"; // drives Is1099Tracked default
+    public bool    Is1099Tracked     { get; set; } = true;
+    public string? TinType           { get; set; }              // "SSN" | "EIN"
+    public string? TinEncrypted      { get; set; }              // Data-Protection ciphertext
+    public string? TinLast4          { get; set; }
+    public string? AddressLine1      { get; set; }
+    public string? AddressLine2      { get; set; }
+    public string? City              { get; set; }
+    public string? State             { get; set; }
+    public string? Zip               { get; set; }
+    public string? Email             { get; set; }
+    public string? Phone             { get; set; }
+    public string  W9Status          { get; set; } = Form1099.W9Status.Missing;
+    public DateOnly? W9ReceivedDate  { get; set; }
+    public string? W9BlobPath        { get; set; }
+    public bool    IsActive          { get; set; } = true;
+    public string? Notes             { get; set; }
+}

API/ROLAC.API/Migrations/20260625200631_AddChurchAiSettings.cs

@@ -0,0 +1,76 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace ROLAC.API.Migrations
+{
+    /// <inheritdoc />
+    public partial class AddChurchAiSettings : Migration
+    {
+        /// <inheritdoc />
+        protected override void Up(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.AddColumn<string>(
+                name: "AiProvider",
+                table: "ChurchProfiles",
+                type: "character varying(20)",
+                maxLength: 20,
+                nullable: false,
+                defaultValue: "Claude");
+
+            migrationBuilder.AddColumn<string>(
+                name: "ClaudeApiKey",
+                table: "ChurchProfiles",
+                type: "character varying(500)",
+                maxLength: 500,
+                nullable: true);
+
+            migrationBuilder.AddColumn<string>(
+                name: "ClaudeModel",
+                table: "ChurchProfiles",
+                type: "character varying(100)",
+                maxLength: 100,
+                nullable: true,
+                defaultValue: "claude-haiku-4-5-20251001");
+
+            migrationBuilder.AddColumn<string>(
+                name: "GeminiApiKey",
+                table: "ChurchProfiles",
+                type: "character varying(500)",
+                maxLength: 500,
+                nullable: true);
+
+            migrationBuilder.AddColumn<string>(
+                name: "GeminiModel",
+                table: "ChurchProfiles",
+                type: "character varying(100)",
+                maxLength: 100,
+                nullable: true,
+                defaultValue: "gemini-2.5-flash-lite");
+        }
+
+        /// <inheritdoc />
+        protected override void Down(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.DropColumn(
+                name: "AiProvider",
+                table: "ChurchProfiles");
+
+            migrationBuilder.DropColumn(
+                name: "ClaudeApiKey",
+                table: "ChurchProfiles");
+
+            migrationBuilder.DropColumn(
+                name: "ClaudeModel",
+                table: "ChurchProfiles");
+
+            migrationBuilder.DropColumn(
+                name: "GeminiApiKey",
+                table: "ChurchProfiles");
+
+            migrationBuilder.DropColumn(
+                name: "GeminiModel",
+                table: "ChurchProfiles");
+        }
+    }
+}

API/ROLAC.API/Migrations/20260625215722_AddExpenseSnapshots.cs

@@ -0,0 +1,122 @@
+using System;
+using Microsoft.EntityFrameworkCore.Migrations;
+using Npgsql.EntityFrameworkCore.PostgreSQL.Metadata;
+
+#nullable disable
+
+namespace ROLAC.API.Migrations
+{
+    /// <inheritdoc />
+    public partial class AddExpenseSnapshots : Migration
+    {
+        /// <inheritdoc />
+        protected override void Up(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.CreateTable(
+                name: "ExpenseSnapshots",
+                columns: table => new
+                {
+                    Id = table.Column<int>(type: "integer", nullable: false)
+                        .Annotation("Npgsql:ValueGenerationStrategy", NpgsqlValueGenerationStrategy.IdentityByDefaultColumn),
+                    Name = table.Column<string>(type: "character varying(150)", maxLength: 150, nullable: false),
+                    MinistryId = table.Column<int>(type: "integer", nullable: false),
+                    Description = table.Column<string>(type: "character varying(500)", maxLength: 500, nullable: false),
+                    VendorName = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    CheckNumber = table.Column<string>(type: "character varying(50)", maxLength: 50, nullable: true),
+                    Notes = table.Column<string>(type: "text", nullable: true),
+                    CreatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    CreatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    UpdatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    UpdatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    IsDeleted = table.Column<bool>(type: "boolean", nullable: false),
+                    DeletedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: true),
+                    DeletedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: true)
+                },
+                constraints: table =>
+                {
+                    table.PrimaryKey("PK_ExpenseSnapshots", x => x.Id);
+                    table.ForeignKey(
+                        name: "FK_ExpenseSnapshots_Ministries_MinistryId",
+                        column: x => x.MinistryId,
+                        principalTable: "Ministries",
+                        principalColumn: "Id",
+                        onDelete: ReferentialAction.Restrict);
+                });
+
+            migrationBuilder.CreateTable(
+                name: "ExpenseSnapshotLines",
+                columns: table => new
+                {
+                    Id = table.Column<int>(type: "integer", nullable: false)
+                        .Annotation("Npgsql:ValueGenerationStrategy", NpgsqlValueGenerationStrategy.IdentityByDefaultColumn),
+                    SnapshotId = table.Column<int>(type: "integer", nullable: false),
+                    CategoryGroupId = table.Column<int>(type: "integer", nullable: false),
+                    SubCategoryId = table.Column<int>(type: "integer", nullable: false),
+                    FunctionalClass = table.Column<string>(type: "character varying(20)", maxLength: 20, nullable: true),
+                    Amount = table.Column<decimal>(type: "numeric(18,2)", nullable: false),
+                    Description = table.Column<string>(type: "character varying(500)", maxLength: 500, nullable: true),
+                    CreatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    CreatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    UpdatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    UpdatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false)
+                },
+                constraints: table =>
+                {
+                    table.PrimaryKey("PK_ExpenseSnapshotLines", x => x.Id);
+                    table.ForeignKey(
+                        name: "FK_ExpenseSnapshotLines_ExpenseCategoryGroups_CategoryGroupId",
+                        column: x => x.CategoryGroupId,
+                        principalTable: "ExpenseCategoryGroups",
+                        principalColumn: "Id",
+                        onDelete: ReferentialAction.Restrict);
+                    table.ForeignKey(
+                        name: "FK_ExpenseSnapshotLines_ExpenseSnapshots_SnapshotId",
+                        column: x => x.SnapshotId,
+                        principalTable: "ExpenseSnapshots",
+                        principalColumn: "Id",
+                        onDelete: ReferentialAction.Cascade);
+                    table.ForeignKey(
+                        name: "FK_ExpenseSnapshotLines_ExpenseSubCategories_SubCategoryId",
+                        column: x => x.SubCategoryId,
+                        principalTable: "ExpenseSubCategories",
+                        principalColumn: "Id",
+                        onDelete: ReferentialAction.Restrict);
+                });
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSnapshotLines_CategoryGroupId",
+                table: "ExpenseSnapshotLines",
+                column: "CategoryGroupId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSnapshotLines_SnapshotId",
+                table: "ExpenseSnapshotLines",
+                column: "SnapshotId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSnapshotLines_SubCategoryId",
+                table: "ExpenseSnapshotLines",
+                column: "SubCategoryId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSnapshots_CreatedAt",
+                table: "ExpenseSnapshots",
+                column: "CreatedAt");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSnapshots_MinistryId",
+                table: "ExpenseSnapshots",
+                column: "MinistryId");
+        }
+
+        /// <inheritdoc />
+        protected override void Down(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.DropTable(
+                name: "ExpenseSnapshotLines");
+
+            migrationBuilder.DropTable(
+                name: "ExpenseSnapshots");
+        }
+    }
+}

API/ROLAC.API/Migrations/20260626001416_AddForm1099RecipientTracking.cs

@@ -0,0 +1,197 @@
+using System;
+using Microsoft.EntityFrameworkCore.Migrations;
+using Npgsql.EntityFrameworkCore.PostgreSQL.Metadata;
+
+#nullable disable
+
+namespace ROLAC.API.Migrations
+{
+    /// <inheritdoc />
+    public partial class AddForm1099RecipientTracking : Migration
+    {
+        /// <inheritdoc />
+        protected override void Up(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.AddColumn<int>(
+                name: "Form1099BoxId",
+                table: "ExpenseSubCategories",
+                type: "integer",
+                nullable: true);
+
+            migrationBuilder.AddColumn<int>(
+                name: "PayeeId",
+                table: "Expenses",
+                type: "integer",
+                nullable: true);
+
+            migrationBuilder.AddColumn<int>(
+                name: "Form1099BoxId",
+                table: "ExpenseCategoryGroups",
+                type: "integer",
+                nullable: true);
+
+            migrationBuilder.CreateTable(
+                name: "Form1099Boxes",
+                columns: table => new
+                {
+                    Id = table.Column<int>(type: "integer", nullable: false)
+                        .Annotation("Npgsql:ValueGenerationStrategy", NpgsqlValueGenerationStrategy.IdentityByDefaultColumn),
+                    BoxCode = table.Column<string>(type: "character varying(10)", maxLength: 10, nullable: false),
+                    Name_en = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: false),
+                    Name_zh = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    FormType = table.Column<string>(type: "character varying(20)", maxLength: 20, nullable: false),
+                    SortOrder = table.Column<int>(type: "integer", nullable: false),
+                    IsActive = table.Column<bool>(type: "boolean", nullable: false),
+                    CreatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    CreatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    UpdatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    UpdatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false)
+                },
+                constraints: table =>
+                {
+                    table.PrimaryKey("PK_Form1099Boxes", x => x.Id);
+                });
+
+            migrationBuilder.CreateTable(
+                name: "Payee1099s",
+                columns: table => new
+                {
+                    Id = table.Column<int>(type: "integer", nullable: false)
+                        .Annotation("Npgsql:ValueGenerationStrategy", NpgsqlValueGenerationStrategy.IdentityByDefaultColumn),
+                    LegalName = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: false),
+                    DisplayName = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    MemberId = table.Column<int>(type: "integer", nullable: true),
+                    TaxClassification = table.Column<string>(type: "character varying(40)", maxLength: 40, nullable: false),
+                    Is1099Tracked = table.Column<bool>(type: "boolean", nullable: false),
+                    TinType = table.Column<string>(type: "character varying(10)", maxLength: 10, nullable: true),
+                    TinEncrypted = table.Column<string>(type: "character varying(500)", maxLength: 500, nullable: true),
+                    TinLast4 = table.Column<string>(type: "character varying(4)", maxLength: 4, nullable: true),
+                    AddressLine1 = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    AddressLine2 = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    City = table.Column<string>(type: "character varying(100)", maxLength: 100, nullable: true),
+                    State = table.Column<string>(type: "character varying(2)", maxLength: 2, nullable: true),
+                    Zip = table.Column<string>(type: "character varying(10)", maxLength: 10, nullable: true),
+                    Email = table.Column<string>(type: "character varying(200)", maxLength: 200, nullable: true),
+                    Phone = table.Column<string>(type: "character varying(30)", maxLength: 30, nullable: true),
+                    W9Status = table.Column<string>(type: "character varying(20)", maxLength: 20, nullable: false, defaultValue: "Missing"),
+                    W9ReceivedDate = table.Column<DateOnly>(type: "date", nullable: true),
+                    W9BlobPath = table.Column<string>(type: "character varying(500)", maxLength: 500, nullable: true),
+                    IsActive = table.Column<bool>(type: "boolean", nullable: false),
+                    Notes = table.Column<string>(type: "character varying(500)", maxLength: 500, nullable: true),
+                    CreatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    CreatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    UpdatedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: false),
+                    UpdatedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: false),
+                    IsDeleted = table.Column<bool>(type: "boolean", nullable: false),
+                    DeletedAt = table.Column<DateTimeOffset>(type: "timestamp with time zone", nullable: true),
+                    DeletedBy = table.Column<string>(type: "character varying(450)", maxLength: 450, nullable: true)
+                },
+                constraints: table =>
+                {
+                    table.PrimaryKey("PK_Payee1099s", x => x.Id);
+                    table.ForeignKey(
+                        name: "FK_Payee1099s_Members_MemberId",
+                        column: x => x.MemberId,
+                        principalTable: "Members",
+                        principalColumn: "Id",
+                        onDelete: ReferentialAction.SetNull);
+                });
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseSubCategories_Form1099BoxId",
+                table: "ExpenseSubCategories",
+                column: "Form1099BoxId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_Expenses_PayeeId",
+                table: "Expenses",
+                column: "PayeeId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_ExpenseCategoryGroups_Form1099BoxId",
+                table: "ExpenseCategoryGroups",
+                column: "Form1099BoxId");
+
+            migrationBuilder.CreateIndex(
+                name: "IX_Form1099Boxes_BoxCode",
+                table: "Form1099Boxes",
+                column: "BoxCode",
+                unique: true);
+
+            migrationBuilder.CreateIndex(
+                name: "IX_Payee1099s_MemberId",
+                table: "Payee1099s",
+                column: "MemberId");
+
+            migrationBuilder.AddForeignKey(
+                name: "FK_ExpenseCategoryGroups_Form1099Boxes_Form1099BoxId",
+                table: "ExpenseCategoryGroups",
+                column: "Form1099BoxId",
+                principalTable: "Form1099Boxes",
+                principalColumn: "Id",
+                onDelete: ReferentialAction.SetNull);
+
+            migrationBuilder.AddForeignKey(
+                name: "FK_Expenses_Payee1099s_PayeeId",
+                table: "Expenses",
+                column: "PayeeId",
+                principalTable: "Payee1099s",
+                principalColumn: "Id",
+                onDelete: ReferentialAction.SetNull);
+
+            migrationBuilder.AddForeignKey(
+                name: "FK_ExpenseSubCategories_Form1099Boxes_Form1099BoxId",
+                table: "ExpenseSubCategories",
+                column: "Form1099BoxId",
+                principalTable: "Form1099Boxes",
+                principalColumn: "Id",
+                onDelete: ReferentialAction.SetNull);
+        }
+
+        /// <inheritdoc />
+        protected override void Down(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.DropForeignKey(
+                name: "FK_ExpenseCategoryGroups_Form1099Boxes_Form1099BoxId",
+                table: "ExpenseCategoryGroups");
+
+            migrationBuilder.DropForeignKey(
+                name: "FK_Expenses_Payee1099s_PayeeId",
+                table: "Expenses");
+
+            migrationBuilder.DropForeignKey(
+                name: "FK_ExpenseSubCategories_Form1099Boxes_Form1099BoxId",
+                table: "ExpenseSubCategories");
+
+            migrationBuilder.DropTable(
+                name: "Form1099Boxes");
+
+            migrationBuilder.DropTable(
+                name: "Payee1099s");
+
+            migrationBuilder.DropIndex(
+                name: "IX_ExpenseSubCategories_Form1099BoxId",
+                table: "ExpenseSubCategories");
+
+            migrationBuilder.DropIndex(
+                name: "IX_Expenses_PayeeId",
+                table: "Expenses");
+
+            migrationBuilder.DropIndex(
+                name: "IX_ExpenseCategoryGroups_Form1099BoxId",
+                table: "ExpenseCategoryGroups");
+
+            migrationBuilder.DropColumn(
+                name: "Form1099BoxId",
+                table: "ExpenseSubCategories");
+
+            migrationBuilder.DropColumn(
+                name: "PayeeId",
+                table: "Expenses");
+
+            migrationBuilder.DropColumn(
+                name: "Form1099BoxId",
+                table: "ExpenseCategoryGroups");
+        }
+    }
+}

API/ROLAC.API/Migrations/20260626012205_AddPayerEinToChurchProfile.cs

@@ -0,0 +1,29 @@
+using Microsoft.EntityFrameworkCore.Migrations;
+
+#nullable disable
+
+namespace ROLAC.API.Migrations
+{
+    /// <inheritdoc />
+    public partial class AddPayerEinToChurchProfile : Migration
+    {
+        /// <inheritdoc />
+        protected override void Up(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.AddColumn<string>(
+                name: "PayerEin",
+                table: "ChurchProfiles",
+                type: "character varying(20)",
+                maxLength: 20,
+                nullable: true);
+        }
+
+        /// <inheritdoc />
+        protected override void Down(MigrationBuilder migrationBuilder)
+        {
+            migrationBuilder.DropColumn(
+                name: "PayerEin",
+                table: "ChurchProfiles");
+        }
+    }
+}

API/ROLAC.API/Migrations/AppDbContextModelSnapshot.cs

@@ -439,6 +439,13 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(500)
                         .HasColumnType("character varying(500)");
 
+                    b.Property<string>("AiProvider")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)")
+                        .HasDefaultValue("Claude");
+
                     b.Property<string>("BankAccountNumber")
                         .HasMaxLength(50)
                         .HasColumnType("character varying(50)");
@@ -455,6 +462,16 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(100)
                         .HasColumnType("character varying(100)");
 
+                    b.Property<string>("ClaudeApiKey")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<string>("ClaudeModel")
+                        .ValueGeneratedOnAdd()
+                        .HasMaxLength(100)
+                        .HasColumnType("character varying(100)")
+                        .HasDefaultValue("claude-haiku-4-5-20251001");
+
                     b.Property<DateTimeOffset>("CreatedAt")
                         .HasColumnType("timestamp with time zone");
 
@@ -467,6 +484,16 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(200)
                         .HasColumnType("character varying(200)");
 
+                    b.Property<string>("GeminiApiKey")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<string>("GeminiModel")
+                        .ValueGeneratedOnAdd()
+                        .HasMaxLength(100)
+                        .HasColumnType("character varying(100)")
+                        .HasDefaultValue("gemini-2.5-flash-lite");
+
                     b.Property<string>("Name")
                         .IsRequired()
                         .HasMaxLength(200)
@@ -479,6 +506,10 @@ namespace ROLAC.API.Migrations
                     b.Property<int>("NextCheckNumber")
                         .HasColumnType("integer");
 
+                    b.Property<string>("PayerEin")
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)");
+
                     b.Property<string>("Phone")
                         .HasMaxLength(50)
                         .HasColumnType("character varying(50)");
@@ -525,9 +556,6 @@ namespace ROLAC.API.Migrations
                     b.Property<decimal>("Amount")
                         .HasColumnType("decimal(18,2)");
 
-                    b.Property<int>("CategoryGroupId")
-                        .HasColumnType("integer");
-
                     b.Property<string>("CheckNumber")
                         .HasMaxLength(50)
                         .HasColumnType("character varying(50)");
@@ -555,10 +583,6 @@ namespace ROLAC.API.Migrations
                     b.Property<DateOnly>("ExpenseDate")
                         .HasColumnType("date");
 
-                    b.Property<string>("FunctionalClass")
-                        .HasMaxLength(20)
-                        .HasColumnType("character varying(20)");
-
                     b.Property<bool>("IsDeleted")
                         .HasColumnType("boolean");
 
@@ -578,6 +602,9 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(450)
                         .HasColumnType("character varying(450)");
 
+                    b.Property<int?>("PayeeId")
+                        .HasColumnType("integer");
+
                     b.Property<string>("ReceiptBlobPath")
                         .HasMaxLength(500)
                         .HasColumnType("character varying(500)");
@@ -600,9 +627,6 @@ namespace ROLAC.API.Migrations
                         .HasColumnType("character varying(30)")
                         .HasDefaultValue("Draft");
 
-                    b.Property<int>("SubCategoryId")
-                        .HasColumnType("integer");
-
                     b.Property<DateTimeOffset?>("SubmittedAt")
                         .HasColumnType("timestamp with time zone");
 
@@ -629,19 +653,17 @@ namespace ROLAC.API.Migrations
 
                     b.HasKey("Id");
 
-                    b.HasIndex("CategoryGroupId");
-
                     b.HasIndex("ExpenseDate");
 
                     b.HasIndex("MemberId");
 
                     b.HasIndex("MinistryId");
 
+                    b.HasIndex("PayeeId");
+
                     b.HasIndex("Status")
                         .HasFilter("\"IsDeleted\" = false");
 
-                    b.HasIndex("SubCategoryId");
-
                     b.ToTable("Expenses");
                 });
 
@@ -661,6 +683,9 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(450)
                         .HasColumnType("character varying(450)");
 
+                    b.Property<int?>("Form1099BoxId")
+                        .HasColumnType("integer");
+
                     b.Property<int?>("Form990LineId")
                         .HasColumnType("integer");
 
@@ -689,11 +714,190 @@ namespace ROLAC.API.Migrations
 
                     b.HasKey("Id");
 
+                    b.HasIndex("Form1099BoxId");
+
                     b.HasIndex("Form990LineId");
 
                     b.ToTable("ExpenseCategoryGroups");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseLine", b =>
+                {
+                    b.Property<int>("Id")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("integer");
+
+                    NpgsqlPropertyBuilderExtensions.UseIdentityByDefaultColumn(b.Property<int>("Id"));
+
+                    b.Property<decimal>("Amount")
+                        .HasColumnType("decimal(18,2)");
+
+                    b.Property<int>("CategoryGroupId")
+                        .HasColumnType("integer");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("CreatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("Description")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<int>("ExpenseId")
+                        .HasColumnType("integer");
+
+                    b.Property<string>("FunctionalClass")
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)");
+
+                    b.Property<int>("SubCategoryId")
+                        .HasColumnType("integer");
+
+                    b.Property<DateTimeOffset>("UpdatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("UpdatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("CategoryGroupId");
+
+                    b.HasIndex("ExpenseId");
+
+                    b.HasIndex("SubCategoryId");
+
+                    b.ToTable("ExpenseLines");
+                });
+
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseSnapshot", b =>
+                {
+                    b.Property<int>("Id")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("integer");
+
+                    NpgsqlPropertyBuilderExtensions.UseIdentityByDefaultColumn(b.Property<int>("Id"));
+
+                    b.Property<string>("CheckNumber")
+                        .HasMaxLength(50)
+                        .HasColumnType("character varying(50)");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("CreatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<DateTimeOffset?>("DeletedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("DeletedBy")
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("Description")
+                        .IsRequired()
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<bool>("IsDeleted")
+                        .HasColumnType("boolean");
+
+                    b.Property<int>("MinistryId")
+                        .HasColumnType("integer");
+
+                    b.Property<string>("Name")
+                        .IsRequired()
+                        .HasMaxLength(150)
+                        .HasColumnType("character varying(150)");
+
+                    b.Property<string>("Notes")
+                        .HasColumnType("text");
+
+                    b.Property<DateTimeOffset>("UpdatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("UpdatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("VendorName")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("CreatedAt");
+
+                    b.HasIndex("MinistryId");
+
+                    b.ToTable("ExpenseSnapshots");
+                });
+
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseSnapshotLine", b =>
+                {
+                    b.Property<int>("Id")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("integer");
+
+                    NpgsqlPropertyBuilderExtensions.UseIdentityByDefaultColumn(b.Property<int>("Id"));
+
+                    b.Property<decimal>("Amount")
+                        .HasColumnType("decimal(18,2)");
+
+                    b.Property<int>("CategoryGroupId")
+                        .HasColumnType("integer");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("CreatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("Description")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<string>("FunctionalClass")
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)");
+
+                    b.Property<int>("SnapshotId")
+                        .HasColumnType("integer");
+
+                    b.Property<int>("SubCategoryId")
+                        .HasColumnType("integer");
+
+                    b.Property<DateTimeOffset>("UpdatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("UpdatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("CategoryGroupId");
+
+                    b.HasIndex("SnapshotId");
+
+                    b.HasIndex("SubCategoryId");
+
+                    b.ToTable("ExpenseSnapshotLines");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.ExpenseSubCategory", b =>
                 {
                     b.Property<int>("Id")
@@ -710,6 +914,9 @@ namespace ROLAC.API.Migrations
                         .HasMaxLength(450)
                         .HasColumnType("character varying(450)");
 
+                    b.Property<int?>("Form1099BoxId")
+                        .HasColumnType("integer");
+
                     b.Property<int?>("Form990LineId")
                         .HasColumnType("integer");
 
@@ -741,6 +948,8 @@ namespace ROLAC.API.Migrations
 
                     b.HasKey("Id");
 
+                    b.HasIndex("Form1099BoxId");
+
                     b.HasIndex("Form990LineId");
 
                     b.HasIndex("GroupId");
@@ -786,6 +995,63 @@ namespace ROLAC.API.Migrations
                     b.ToTable("FamilyUnits");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.Form1099Box", b =>
+                {
+                    b.Property<int>("Id")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("integer");
+
+                    NpgsqlPropertyBuilderExtensions.UseIdentityByDefaultColumn(b.Property<int>("Id"));
+
+                    b.Property<string>("BoxCode")
+                        .IsRequired()
+                        .HasMaxLength(10)
+                        .HasColumnType("character varying(10)");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("CreatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("FormType")
+                        .IsRequired()
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)");
+
+                    b.Property<bool>("IsActive")
+                        .HasColumnType("boolean");
+
+                    b.Property<string>("Name_en")
+                        .IsRequired()
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<string>("Name_zh")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<int>("SortOrder")
+                        .HasColumnType("integer");
+
+                    b.Property<DateTimeOffset>("UpdatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("UpdatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("BoxCode")
+                        .IsUnique();
+
+                    b.ToTable("Form1099Boxes");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.Form990ExpenseLine", b =>
                 {
                     b.Property<int>("Id")
@@ -1735,6 +2001,128 @@ namespace ROLAC.API.Migrations
                     b.ToTable("OfferingSessions");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.Payee1099", b =>
+                {
+                    b.Property<int>("Id")
+                        .ValueGeneratedOnAdd()
+                        .HasColumnType("integer");
+
+                    NpgsqlPropertyBuilderExtensions.UseIdentityByDefaultColumn(b.Property<int>("Id"));
+
+                    b.Property<string>("AddressLine1")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<string>("AddressLine2")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<string>("City")
+                        .HasMaxLength(100)
+                        .HasColumnType("character varying(100)");
+
+                    b.Property<DateTimeOffset>("CreatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("CreatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<DateTimeOffset?>("DeletedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("DeletedBy")
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("DisplayName")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<string>("Email")
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<bool>("Is1099Tracked")
+                        .HasColumnType("boolean");
+
+                    b.Property<bool>("IsActive")
+                        .HasColumnType("boolean");
+
+                    b.Property<bool>("IsDeleted")
+                        .HasColumnType("boolean");
+
+                    b.Property<string>("LegalName")
+                        .IsRequired()
+                        .HasMaxLength(200)
+                        .HasColumnType("character varying(200)");
+
+                    b.Property<int?>("MemberId")
+                        .HasColumnType("integer");
+
+                    b.Property<string>("Notes")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<string>("Phone")
+                        .HasMaxLength(30)
+                        .HasColumnType("character varying(30)");
+
+                    b.Property<string>("State")
+                        .HasMaxLength(2)
+                        .HasColumnType("character varying(2)");
+
+                    b.Property<string>("TaxClassification")
+                        .IsRequired()
+                        .HasMaxLength(40)
+                        .HasColumnType("character varying(40)");
+
+                    b.Property<string>("TinEncrypted")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<string>("TinLast4")
+                        .HasMaxLength(4)
+                        .HasColumnType("character varying(4)");
+
+                    b.Property<string>("TinType")
+                        .HasMaxLength(10)
+                        .HasColumnType("character varying(10)");
+
+                    b.Property<DateTimeOffset>("UpdatedAt")
+                        .HasColumnType("timestamp with time zone");
+
+                    b.Property<string>("UpdatedBy")
+                        .IsRequired()
+                        .HasMaxLength(450)
+                        .HasColumnType("character varying(450)");
+
+                    b.Property<string>("W9BlobPath")
+                        .HasMaxLength(500)
+                        .HasColumnType("character varying(500)");
+
+                    b.Property<DateOnly?>("W9ReceivedDate")
+                        .HasColumnType("date");
+
+                    b.Property<string>("W9Status")
+                        .IsRequired()
+                        .ValueGeneratedOnAdd()
+                        .HasMaxLength(20)
+                        .HasColumnType("character varying(20)")
+                        .HasDefaultValue("Missing");
+
+                    b.Property<string>("Zip")
+                        .HasMaxLength(10)
+                        .HasColumnType("character varying(10)");
+
+                    b.HasKey("Id");
+
+                    b.HasIndex("MemberId");
+
+                    b.ToTable("Payee1099s");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.RefreshToken", b =>
                 {
                     b.Property<int>("Id")
@@ -2007,12 +2395,6 @@ namespace ROLAC.API.Migrations
 
             modelBuilder.Entity("ROLAC.API.Entities.Expense", b =>
                 {
-                    b.HasOne("ROLAC.API.Entities.ExpenseCategoryGroup", "CategoryGroup")
-                        .WithMany()
-                        .HasForeignKey("CategoryGroupId")
-                        .OnDelete(DeleteBehavior.Restrict)
-                        .IsRequired();
-
                     b.HasOne("ROLAC.API.Entities.Member", "Member")
                         .WithMany()
                         .HasForeignKey("MemberId")
@@ -2024,6 +2406,49 @@ namespace ROLAC.API.Migrations
                         .OnDelete(DeleteBehavior.Restrict)
                         .IsRequired();
 
+                    b.HasOne("ROLAC.API.Entities.Payee1099", "Payee")
+                        .WithMany()
+                        .HasForeignKey("PayeeId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
+                    b.Navigation("Member");
+
+                    b.Navigation("Ministry");
+
+                    b.Navigation("Payee");
+                });
+
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseCategoryGroup", b =>
+                {
+                    b.HasOne("ROLAC.API.Entities.Form1099Box", "Form1099Box")
+                        .WithMany()
+                        .HasForeignKey("Form1099BoxId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
+                    b.HasOne("ROLAC.API.Entities.Form990ExpenseLine", "Form990Line")
+                        .WithMany()
+                        .HasForeignKey("Form990LineId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
+                    b.Navigation("Form1099Box");
+
+                    b.Navigation("Form990Line");
+                });
+
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseLine", b =>
+                {
+                    b.HasOne("ROLAC.API.Entities.ExpenseCategoryGroup", "CategoryGroup")
+                        .WithMany()
+                        .HasForeignKey("CategoryGroupId")
+                        .OnDelete(DeleteBehavior.Restrict)
+                        .IsRequired();
+
+                    b.HasOne("ROLAC.API.Entities.Expense", "Expense")
+                        .WithMany("Lines")
+                        .HasForeignKey("ExpenseId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
                     b.HasOne("ROLAC.API.Entities.ExpenseSubCategory", "SubCategory")
                         .WithMany()
                         .HasForeignKey("SubCategoryId")
@@ -2032,25 +2457,56 @@ namespace ROLAC.API.Migrations
 
                     b.Navigation("CategoryGroup");
 
-                    b.Navigation("Member");
+                    b.Navigation("Expense");
-
-                    b.Navigation("Ministry");
 
                     b.Navigation("SubCategory");
                 });
 
-            modelBuilder.Entity("ROLAC.API.Entities.ExpenseCategoryGroup", b =>
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseSnapshot", b =>
                 {
-                    b.HasOne("ROLAC.API.Entities.Form990ExpenseLine", "Form990Line")
+                    b.HasOne("ROLAC.API.Entities.Ministry", "Ministry")
                         .WithMany()
-                        .HasForeignKey("Form990LineId")
+                        .HasForeignKey("MinistryId")
-                        .OnDelete(DeleteBehavior.SetNull);
+                        .OnDelete(DeleteBehavior.Restrict)
+                        .IsRequired();
 
-                    b.Navigation("Form990Line");
+                    b.Navigation("Ministry");
+                });
+
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseSnapshotLine", b =>
+                {
+                    b.HasOne("ROLAC.API.Entities.ExpenseCategoryGroup", "CategoryGroup")
+                        .WithMany()
+                        .HasForeignKey("CategoryGroupId")
+                        .OnDelete(DeleteBehavior.Restrict)
+                        .IsRequired();
+
+                    b.HasOne("ROLAC.API.Entities.ExpenseSnapshot", "Snapshot")
+                        .WithMany("Lines")
+                        .HasForeignKey("SnapshotId")
+                        .OnDelete(DeleteBehavior.Cascade)
+                        .IsRequired();
+
+                    b.HasOne("ROLAC.API.Entities.ExpenseSubCategory", "SubCategory")
+                        .WithMany()
+                        .HasForeignKey("SubCategoryId")
+                        .OnDelete(DeleteBehavior.Restrict)
+                        .IsRequired();
+
+                    b.Navigation("CategoryGroup");
+
+                    b.Navigation("Snapshot");
+
+                    b.Navigation("SubCategory");
                 });
 
             modelBuilder.Entity("ROLAC.API.Entities.ExpenseSubCategory", b =>
                 {
+                    b.HasOne("ROLAC.API.Entities.Form1099Box", "Form1099Box")
+                        .WithMany()
+                        .HasForeignKey("Form1099BoxId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
                     b.HasOne("ROLAC.API.Entities.Form990ExpenseLine", "Form990Line")
                         .WithMany()
                         .HasForeignKey("Form990LineId")
@@ -2062,6 +2518,8 @@ namespace ROLAC.API.Migrations
                         .OnDelete(DeleteBehavior.Restrict)
                         .IsRequired();
 
+                    b.Navigation("Form1099Box");
+
                     b.Navigation("Form990Line");
 
                     b.Navigation("Group");
@@ -2141,6 +2599,16 @@ namespace ROLAC.API.Migrations
                     b.Navigation("MessagingGroup");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.Payee1099", b =>
+                {
+                    b.HasOne("ROLAC.API.Entities.Member", "Member")
+                        .WithMany()
+                        .HasForeignKey("MemberId")
+                        .OnDelete(DeleteBehavior.SetNull);
+
+                    b.Navigation("Member");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.RefreshToken", b =>
                 {
                     b.HasOne("ROLAC.API.Entities.AppUser", "User")
@@ -2184,11 +2652,21 @@ namespace ROLAC.API.Migrations
                     b.Navigation("Lines");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.Expense", b =>
+                {
+                    b.Navigation("Lines");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.ExpenseCategoryGroup", b =>
                 {
                     b.Navigation("SubCategories");
                 });
 
+            modelBuilder.Entity("ROLAC.API.Entities.ExpenseSnapshot", b =>
+                {
+                    b.Navigation("Lines");
+                });
+
             modelBuilder.Entity("ROLAC.API.Entities.OfferingSession", b =>
                 {
                     b.Navigation("Givings");

API/ROLAC.API/Program.cs

@@ -15,6 +15,7 @@ using ROLAC.API.Json;
 using ROLAC.API.Middleware;
 using ROLAC.API.Services;
 using ROLAC.API.Services.Logging;
+using ROLAC.API.Services.Security;
 
 var builder = WebApplication.CreateBuilder(args);
 var config  = builder.Configuration;
@@ -153,14 +154,23 @@ builder.Services.AddScoped<ROLAC.API.Services.Storage.IFileStorage,
                            ROLAC.API.Services.Storage.LocalDiskFileStorage>();
 builder.Services.AddScoped<IExpenseCategoryService, ExpenseCategoryService>();
 builder.Services.AddScoped<IExpenseService, ExpenseService>();
+builder.Services.AddScoped<IExpenseSnapshotService, ExpenseSnapshotService>();
 builder.Services.AddScoped<IMonthlyStatementService, MonthlyStatementService>();
 builder.Services.AddScoped<IFinanceDashboardService, FinanceDashboardService>();
 builder.Services.AddScoped<IForm990ReportService, Form990ReportService>();
+builder.Services.AddScoped<IForm1099ReportService, Form1099ReportService>();
+builder.Services.AddScoped<IPayee1099Service, Payee1099Service>();
+builder.Services.AddScoped<I1099FormService, Form1099FormService>();
+builder.Services.AddDataProtection();
+builder.Services.AddScoped<ITinProtector, TinProtector>();
 builder.Services.AddScoped<IChurchProfileService, ChurchProfileService>();
 builder.Services.AddScoped<ISettingsService, SettingsService>();
 builder.Services.AddScoped<IDisbursementService, DisbursementService>();
 builder.Services.AddScoped<ROLAC.API.Services.Disbursement.ICheckPrintService,
                            ROLAC.API.Services.Disbursement.CheckPrintService>();
+// Pre-printed check-stock field coordinates; tune in appsettings.json without recompiling.
+builder.Services.Configure<ROLAC.API.Services.Disbursement.CheckPrintLayoutOptions>(
+    config.GetSection("CheckPrint:Layout"));
 builder.Services.AddScoped<IMealAttendanceService, MealAttendanceService>();
 
 // ── Notifications (email via SMTP + Line) ──────────────────────────────────
@@ -179,6 +189,23 @@ builder.Services.AddScoped<ROLAC.API.Services.Notifications.ILineNotificationSer
 builder.Services.AddHttpClient<ROLAC.API.Services.Notifications.IMessageChannel,
                                ROLAC.API.Services.Notifications.LineMessageChannel>();
 
+// ── AI assist (expense translation + category suggestion) ──────────────────
+// Backend proxy so the API key stays server-side. Provider + model + key come from the
+// ChurchProfile DB record (editable via Church Profile → AI 設定); the factory picks Claude
+// or Gemini per request based on ChurchProfile.AiProvider.
+builder.Services.AddHttpClient<ROLAC.API.Services.Ai.GeminiExpenseAiService>();
+builder.Services.AddHttpClient<ROLAC.API.Services.Ai.ClaudeExpenseAiService>();
+builder.Services.AddScoped<ROLAC.API.Services.Ai.IChurchAiConfigProvider,
+                           ROLAC.API.Services.Ai.ChurchAiConfigProvider>();
+builder.Services.AddScoped<ROLAC.API.Services.Ai.IExpenseAiServiceFactory,
+                           ROLAC.API.Services.Ai.ExpenseAiServiceFactory>();
+
+// Category-mapping AI (define a 大項/小項: refine name + translate + suggest Form 990 line).
+builder.Services.AddHttpClient<ROLAC.API.Services.Ai.GeminiExpenseCategoryAiService>();
+builder.Services.AddHttpClient<ROLAC.API.Services.Ai.ClaudeExpenseCategoryAiService>();
+builder.Services.AddScoped<ROLAC.API.Services.Ai.IExpenseCategoryAiServiceFactory,
+                           ROLAC.API.Services.Ai.ExpenseCategoryAiServiceFactory>();
+
 // ---------------------------------------------------------------------------
 // Configurable role-based permissions (RBAC matrix)
 // ---------------------------------------------------------------------------

API/ROLAC.API/Services/Ai/ChurchAiConfig.cs

@@ -0,0 +1,13 @@
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>Active AI configuration resolved from the ChurchProfile singleton (blanks filled with defaults).</summary>
+public sealed record ChurchAiConfig(
+    string Provider,
+    string ClaudeModel, string? ClaudeApiKey,
+    string GeminiModel, string? GeminiApiKey);
+
+/// <summary>Reads the church's AI settings from the database for the current request.</summary>
+public interface IChurchAiConfigProvider
+{
+    Task<ChurchAiConfig> GetAsync(CancellationToken ct = default);
+}

API/ROLAC.API/Services/Ai/ChurchAiConfigProvider.cs

@@ -0,0 +1,29 @@
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Loads AI settings from the singleton <c>ChurchProfile</c> row, substituting default model names
+/// for any blank field so a freshly migrated install still names a valid model. The API keys are
+/// passed through as-is (null when unset → the calling service treats AI as disabled).
+/// </summary>
+public sealed class ChurchAiConfigProvider : IChurchAiConfigProvider
+{
+    private const string DefaultClaudeModel = "claude-haiku-4-5-20251001";
+    private const string DefaultGeminiModel = "gemini-2.5-flash-lite";
+
+    private readonly AppDbContext _db;
+    public ChurchAiConfigProvider(AppDbContext db) => _db = db;
+
+    public async Task<ChurchAiConfig> GetAsync(CancellationToken ct = default)
+    {
+        var p = await _db.ChurchProfiles.AsNoTracking().OrderBy(x => x.Id).FirstOrDefaultAsync(ct);
+
+        var provider = string.IsNullOrWhiteSpace(p?.AiProvider) ? "Claude" : p.AiProvider;
+        var claudeModel = string.IsNullOrWhiteSpace(p?.ClaudeModel) ? DefaultClaudeModel : p!.ClaudeModel!;
+        var geminiModel = string.IsNullOrWhiteSpace(p?.GeminiModel) ? DefaultGeminiModel : p!.GeminiModel!;
+
+        return new ChurchAiConfig(provider, claudeModel, p?.ClaudeApiKey, geminiModel, p?.GeminiApiKey);
+    }
+}

API/ROLAC.API/Services/Ai/ClaudeExpenseAiService.cs

@@ -0,0 +1,127 @@
+using System.Net.Http.Json;
+using System.Text.Json;
+using ROLAC.API.Data;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Translates and classifies an expense via the Anthropic Claude Messages API. It forces a single
+/// tool call (<c>tool_choice</c> → <c>classify_expense</c>) whose <c>input_schema</c> matches our
+/// answer shape, so the model returns structured JSON in a <c>tool_use</c> block. The catalog,
+/// prompt, and id validation come from <see cref="ExpenseAiServiceBase"/>; this class only owns the
+/// Claude HTTP call + parse. Forced tool use works on every Claude model, so the configured
+/// model can be swapped (e.g. to a cheaper model) without code changes.
+/// </summary>
+public sealed class ClaudeExpenseAiService : ExpenseAiServiceBase
+{
+    private const string BaseUrl          = "https://api.anthropic.com/v1";
+    private const string AnthropicVersion = "2023-06-01";
+
+    private readonly HttpClient _http;
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ILogger<ClaudeExpenseAiService> _logger;
+
+    public ClaudeExpenseAiService(
+        HttpClient http,
+        IChurchAiConfigProvider config,
+        AppDbContext db,
+        ILogger<ClaudeExpenseAiService> logger)
+        : base(db)
+    {
+        _http = http;
+        _config = config;
+        _logger = logger;
+    }
+
+    protected override async Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct)
+    {
+        var cfg = await _config.GetAsync(ct);
+        if (string.IsNullOrWhiteSpace(cfg.ClaudeApiKey))
+        {
+            _logger.LogWarning("Claude API key is not configured; expense AI assist is disabled.");
+            return null;
+        }
+
+        try
+        {
+            var payload = new
+            {
+                model = cfg.ClaudeModel,
+                max_tokens = 1024,
+                tools = new[]
+                {
+                    new
+                    {
+                        name = "classify_expense",
+                        description = "Record the English translation and the chosen expense category ids for the expense.",
+                        input_schema = new
+                        {
+                            type = "object",
+                            properties = new
+                            {
+                                chineseDescription = new { type = "string" },
+                                englishDescription = new { type = "string" },
+                                groupId = new { type = "integer" },
+                                subCategoryId = new { type = "integer" },
+                                confidence = new { type = "number" },
+                            },
+                            required = new[] { "chineseDescription", "englishDescription", "groupId", "subCategoryId", "confidence" },
+                        },
+                    },
+                },
+                tool_choice = new { type = "tool", name = "classify_expense" },
+                messages = new[]
+                {
+                    new { role = "user", content = prompt },
+                },
+            };
+
+            var url = $"{BaseUrl}/messages";
+            using var request = new HttpRequestMessage(HttpMethod.Post, url)
+            {
+                Content = JsonContent.Create(payload),
+            };
+            request.Headers.Add("x-api-key", cfg.ClaudeApiKey);
+            request.Headers.Add("anthropic-version", AnthropicVersion);
+
+            using var response = await _http.SendAsync(request, ct);
+            if (!response.IsSuccessStatusCode)
+            {
+                var body = await response.Content.ReadAsStringAsync(ct);
+                _logger.LogWarning("Claude returned {Status}: {Body}", (int)response.StatusCode, body);
+                return null;
+            }
+
+            // The forced tool call lands in content[] as a tool_use block; its `input` is our object.
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStreamAsync(ct));
+            foreach (var block in doc.RootElement.GetProperty("content").EnumerateArray())
+            {
+                if (block.GetProperty("type").GetString() != "tool_use") continue;
+
+                var parsed = block.GetProperty("input").Deserialize<ClaudeAnswer>(
+                    new JsonSerializerOptions { PropertyNameCaseInsensitive = true });
+                if (parsed is null) return null;
+
+                return new ModelAnswer(parsed.EnglishDescription, parsed.ChineseDescription, parsed.GroupId, parsed.SubCategoryId, parsed.Confidence);
+            }
+
+            _logger.LogWarning("Claude response contained no tool_use block.");
+            return null;
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Claude expense AI assist failed.");
+            return null;
+        }
+    }
+
+    /// <summary>Shape of the classify_expense tool input the model fills in.</summary>
+    private sealed class ClaudeAnswer
+    {
+        public string? EnglishDescription { get; set; }
+        public string? ChineseDescription { get; set; }
+        public int     GroupId            { get; set; }
+        public int     SubCategoryId      { get; set; }
+        public double  Confidence         { get; set; }
+    }
+}

API/ROLAC.API/Services/Ai/ClaudeExpenseCategoryAiService.cs

@@ -0,0 +1,124 @@
+using System.Net.Http.Json;
+using System.Text.Json;
+using ROLAC.API.Data;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Refines, translates, and maps an expense category to a Form 990 line via the Anthropic Claude
+/// Messages API. It forces a single tool call (<c>tool_choice</c> → <c>map_category</c>) whose
+/// <c>input_schema</c> matches our answer shape, so the model returns structured JSON in a
+/// <c>tool_use</c> block. The catalog, prompt, and id validation come from
+/// <see cref="ExpenseCategoryAiServiceBase"/>; this class only owns the Claude HTTP call + parse.
+/// </summary>
+public sealed class ClaudeExpenseCategoryAiService : ExpenseCategoryAiServiceBase
+{
+    private const string BaseUrl          = "https://api.anthropic.com/v1";
+    private const string AnthropicVersion = "2023-06-01";
+
+    private readonly HttpClient _http;
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ILogger<ClaudeExpenseCategoryAiService> _logger;
+
+    public ClaudeExpenseCategoryAiService(
+        HttpClient http,
+        IChurchAiConfigProvider config,
+        AppDbContext db,
+        ILogger<ClaudeExpenseCategoryAiService> logger)
+        : base(db)
+    {
+        _http = http;
+        _config = config;
+        _logger = logger;
+    }
+
+    protected override async Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct)
+    {
+        var cfg = await _config.GetAsync(ct);
+        if (string.IsNullOrWhiteSpace(cfg.ClaudeApiKey))
+        {
+            _logger.LogWarning("Claude API key is not configured; category AI assist is disabled.");
+            return null;
+        }
+
+        try
+        {
+            var payload = new
+            {
+                model = cfg.ClaudeModel,
+                max_tokens = 1024,
+                tools = new[]
+                {
+                    new
+                    {
+                        name = "map_category",
+                        description = "Record the refined Chinese name, English translation, and chosen Form 990 line id for the expense category.",
+                        input_schema = new
+                        {
+                            type = "object",
+                            properties = new
+                            {
+                                chineseName = new { type = "string" },
+                                englishName = new { type = "string" },
+                                form990LineId = new { type = "integer" },
+                                confidence = new { type = "number" },
+                            },
+                            required = new[] { "chineseName", "englishName", "form990LineId", "confidence" },
+                        },
+                    },
+                },
+                tool_choice = new { type = "tool", name = "map_category" },
+                messages = new[]
+                {
+                    new { role = "user", content = prompt },
+                },
+            };
+
+            var url = $"{BaseUrl}/messages";
+            using var request = new HttpRequestMessage(HttpMethod.Post, url)
+            {
+                Content = JsonContent.Create(payload),
+            };
+            request.Headers.Add("x-api-key", cfg.ClaudeApiKey);
+            request.Headers.Add("anthropic-version", AnthropicVersion);
+
+            using var response = await _http.SendAsync(request, ct);
+            if (!response.IsSuccessStatusCode)
+            {
+                var body = await response.Content.ReadAsStringAsync(ct);
+                _logger.LogWarning("Claude returned {Status}: {Body}", (int)response.StatusCode, body);
+                return null;
+            }
+
+            // The forced tool call lands in content[] as a tool_use block; its `input` is our object.
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStreamAsync(ct));
+            foreach (var block in doc.RootElement.GetProperty("content").EnumerateArray())
+            {
+                if (block.GetProperty("type").GetString() != "tool_use") continue;
+
+                var parsed = block.GetProperty("input").Deserialize<ClaudeAnswer>(
+                    new JsonSerializerOptions { PropertyNameCaseInsensitive = true });
+                if (parsed is null) return null;
+
+                return new ModelAnswer(parsed.ChineseName, parsed.EnglishName, parsed.Form990LineId, parsed.Confidence);
+            }
+
+            _logger.LogWarning("Claude response contained no tool_use block.");
+            return null;
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Claude category AI assist failed.");
+            return null;
+        }
+    }
+
+    /// <summary>Shape of the map_category tool input the model fills in.</summary>
+    private sealed class ClaudeAnswer
+    {
+        public string? ChineseName   { get; set; }
+        public string? EnglishName   { get; set; }
+        public int?    Form990LineId { get; set; }
+        public double  Confidence    { get; set; }
+    }
+}

API/ROLAC.API/Services/Ai/ExpenseAiServiceBase.cs

@@ -0,0 +1,119 @@
+using System.Text.Json;
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Expense;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Provider-independent expense-AI logic: loads the active category catalog, builds the
+/// classification prompt, and validates the model's chosen ids against that catalog. Concrete
+/// providers (Gemini, Claude) only implement <see cref="CallModelAsync"/> — the HTTP call plus
+/// response parsing — so the catalog/prompt/validation code lives in exactly one place.
+/// </summary>
+public abstract class ExpenseAiServiceBase : IExpenseAiService
+{
+    private readonly AppDbContext _db;
+
+    protected ExpenseAiServiceBase(AppDbContext db) => _db = db;
+
+    /// <summary>One sub-category in the catalog passed to the model.</summary>
+    protected sealed record CatalogSub(int Id, string NameEn, string? NameZh);
+
+    /// <summary>One major category (with its sub-categories) in the catalog passed to the model.</summary>
+    protected sealed record CatalogGroup(int Id, string NameEn, string? NameZh, IReadOnlyList<CatalogSub> Subs);
+
+    /// <summary>The model's raw answer, before its ids are validated against the catalog.</summary>
+    protected sealed record ModelAnswer(
+        string? EnglishDescription, string? ChineseDescription, int GroupId, int SubCategoryId, double Confidence);
+
+    public async Task<ExpenseAiSuggestion> SuggestAsync(string chineseText, decimal amount, CancellationToken ct = default)
+    {
+        var catalog = await LoadCatalogAsync(ct);
+        var prompt = BuildPrompt(chineseText, amount, catalog);
+
+        var answer = await CallModelAsync(prompt, ct);
+        if (answer is null) return new ExpenseAiSuggestion();
+
+        return BuildSuggestion(answer, catalog);
+    }
+
+    /// <summary>
+    /// Call the provider's API with <paramref name="prompt"/> and return its parsed answer, or null
+    /// on any failure (missing key, HTTP error, unparseable response). Implementations must not throw.
+    /// </summary>
+    protected abstract Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct);
+
+    private async Task<List<CatalogGroup>> LoadCatalogAsync(CancellationToken ct)
+    {
+        return await _db.ExpenseCategoryGroups
+            .AsNoTracking()
+            .Where(group => group.IsActive)
+            .OrderBy(group => group.SortOrder)
+            .Select(group => new CatalogGroup(
+                group.Id,
+                group.Name_en,
+                group.Name_zh,
+                group.SubCategories
+                    .Where(sub => sub.IsActive)
+                    .OrderBy(sub => sub.SortOrder)
+                    .Select(sub => new CatalogSub(sub.Id, sub.Name_en, sub.Name_zh))
+                    .ToList()))
+            .ToListAsync(ct);
+    }
+
+    private static string BuildPrompt(string chineseText, decimal amount, List<CatalogGroup> catalog)
+    {
+        var catalogJson = JsonSerializer.Serialize(catalog);
+        return
+            "You are a bookkeeping assistant for a church. Given an expense description (often in " +
+            "Traditional Chinese) and its amount, do three things:\n" +
+            "1. Correct any typos in the description and refine it into natural Traditional Chinese — " +
+            "return it as chineseDescription.\n" +
+            "2. Translate that into concise, natural accounting English (a short noun phrase, not a " +
+            "full sentence) — return it as englishDescription.\n" +
+            "3. Choose the single best matching major category (group) and sub-category from the catalog " +
+            "below. You MUST pick a groupId and subCategoryId that appear in the catalog, and the " +
+            "subCategoryId must belong to that groupId. If nothing fits well, choose the closest " +
+            "\"Other / 其他\" option and lower your confidence.\n\n" +
+            $"Expense description: {chineseText}\n" +
+            $"Amount: {amount}\n\n" +
+            $"Category catalog (JSON; each group has an Id, English/Chinese names, and its Subs):\n{catalogJson}";
+    }
+
+    private static ExpenseAiSuggestion BuildSuggestion(ModelAnswer answer, List<CatalogGroup> catalog)
+    {
+        var suggestion = new ExpenseAiSuggestion
+        {
+            EnglishDescription = string.IsNullOrWhiteSpace(answer.EnglishDescription)
+                ? null
+                : answer.EnglishDescription.Trim(),
+            ChineseDescription = string.IsNullOrWhiteSpace(answer.ChineseDescription)
+                ? null
+                : answer.ChineseDescription.Trim(),
+            Confidence = answer.Confidence,
+        };
+
+        // Re-validate the returned ids against the catalog; drop anything that doesn't line up
+        // (defends against a hallucinated id, or a sub-category that doesn't belong to the group).
+        var group = catalog.FirstOrDefault(candidate => candidate.Id == answer.GroupId);
+        if (group is not null)
+        {
+            suggestion.GroupId = group.Id;
+            suggestion.GroupLabel = Label(group.NameEn, group.NameZh);
+
+            var sub = group.Subs.FirstOrDefault(candidate => candidate.Id == answer.SubCategoryId);
+            if (sub is not null)
+            {
+                suggestion.SubCategoryId = sub.Id;
+                suggestion.SubLabel = Label(sub.NameEn, sub.NameZh);
+            }
+        }
+
+        return suggestion;
+    }
+
+    /// <summary>Mirror the frontend's bilingual() convention: "English / 中文" (or just English).</summary>
+    private static string Label(string nameEn, string? nameZh)
+        => string.IsNullOrWhiteSpace(nameZh) ? nameEn : $"{nameEn} / {nameZh}";
+}

API/ROLAC.API/Services/Ai/ExpenseAiServiceFactory.cs

@@ -0,0 +1,30 @@
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>Selects the active expense-AI provider per request from <c>ChurchProfile.AiProvider</c>.</summary>
+public interface IExpenseAiServiceFactory
+{
+    Task<IExpenseAiService> ResolveAsync(CancellationToken ct = default);
+}
+
+public sealed class ExpenseAiServiceFactory : IExpenseAiServiceFactory
+{
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ClaudeExpenseAiService _claude;
+    private readonly GeminiExpenseAiService _gemini;
+
+    public ExpenseAiServiceFactory(
+        IChurchAiConfigProvider config,
+        ClaudeExpenseAiService claude,
+        GeminiExpenseAiService gemini)
+    {
+        _config = config;
+        _claude = claude;
+        _gemini = gemini;
+    }
+
+    public async Task<IExpenseAiService> ResolveAsync(CancellationToken ct = default)
+    {
+        var cfg = await _config.GetAsync(ct);
+        return cfg.Provider.Equals("Gemini", StringComparison.OrdinalIgnoreCase) ? _gemini : _claude;
+    }
+}

API/ROLAC.API/Services/Ai/ExpenseCategoryAiServiceBase.cs

@@ -0,0 +1,116 @@
+using System.Text;
+using System.Text.Json;
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Expense;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Provider-independent category-AI logic: loads the active Form 990 line catalog, builds the
+/// mapping prompt, and validates the model's chosen line id against that catalog. Concrete providers
+/// (Gemini, Claude) only implement <see cref="CallModelAsync"/> — the HTTP call plus response parsing —
+/// so the catalog/prompt/validation code lives in exactly one place. Mirrors
+/// <see cref="ExpenseAiServiceBase"/>, which does the same for the expense-entry classification task.
+/// </summary>
+public abstract class ExpenseCategoryAiServiceBase : IExpenseCategoryAiService
+{
+    private readonly AppDbContext _db;
+
+    protected ExpenseCategoryAiServiceBase(AppDbContext db) => _db = db;
+
+    /// <summary>One Form 990 line in the catalog passed to the model.</summary>
+    protected sealed record CatalogLine(int Id, string LineCode, string NameEn, string? NameZh);
+
+    /// <summary>The model's raw answer, before its line id is validated against the catalog.</summary>
+    protected sealed record ModelAnswer(string? ChineseName, string? EnglishName, int? Form990LineId, double Confidence);
+
+    public async Task<CategoryAiSuggestion> SuggestAsync(ExpenseCategoryAiRequest request, CancellationToken ct = default)
+    {
+        var catalog = await LoadCatalogAsync(ct);
+        var prompt = BuildPrompt(request, catalog);
+
+        var answer = await CallModelAsync(prompt, ct);
+        if (answer is null) return new CategoryAiSuggestion();
+
+        return BuildSuggestion(answer, catalog);
+    }
+
+    /// <summary>
+    /// Call the provider's API with <paramref name="prompt"/> and return its parsed answer, or null
+    /// on any failure (missing key, HTTP error, unparseable response). Implementations must not throw.
+    /// </summary>
+    protected abstract Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct);
+
+    private async Task<List<CatalogLine>> LoadCatalogAsync(CancellationToken ct)
+    {
+        return await _db.Form990ExpenseLines
+            .AsNoTracking()
+            .Where(line => line.IsActive)
+            .OrderBy(line => line.SortOrder)
+            .Select(line => new CatalogLine(line.Id, line.LineCode, line.Name_en, line.Name_zh))
+            .ToListAsync(ct);
+    }
+
+    private static string BuildPrompt(ExpenseCategoryAiRequest request, List<CatalogLine> catalog)
+    {
+        var catalogJson = JsonSerializer.Serialize(catalog);
+        var levelLabel = request.Level.Equals("sub", StringComparison.OrdinalIgnoreCase)
+            ? "sub-category (小項)"
+            : "major category (大項)";
+
+        var context = new StringBuilder();
+        context.Append($"This is an expense {levelLabel} in a church's bookkeeping chart of accounts.\n");
+        if (!string.IsNullOrWhiteSpace(request.Name_zh))
+            context.Append($"Chinese name entered: {request.Name_zh}\n");
+        if (!string.IsNullOrWhiteSpace(request.Name_en))
+            context.Append($"English name entered: {request.Name_en}\n");
+        if (!string.IsNullOrWhiteSpace(request.ParentGroupName))
+            context.Append($"It belongs under the parent major category: {request.ParentGroupName}\n");
+        if (request.ParentForm990LineId is int parentLineId)
+            context.Append(
+                $"The parent major category is mapped to Form 990 line id {parentLineId}; prefer a consistent " +
+                "choice unless a more specific line clearly fits this sub-category.\n");
+
+        return
+            "You are a bookkeeping assistant for a church mapping its expense categories to the IRS Form 990 " +
+            "Part IX (Statement of Functional Expenses) lines. Given an expense category name (often in " +
+            "Traditional Chinese), do three things:\n" +
+            "1. Correct any typos in the name and refine it into natural Traditional Chinese — return it as " +
+            "chineseName.\n" +
+            "2. Translate that into a concise, natural accounting English noun phrase (not a full sentence) — " +
+            "return it as englishName.\n" +
+            "3. Choose the single best matching Form 990 line from the catalog below. You MUST pick a " +
+            "form990LineId that appears in the catalog. If nothing fits well, choose the closest general line " +
+            "(e.g. an \"Other expenses\" line) and lower your confidence.\n\n" +
+            context +
+            "\n" +
+            $"Form 990 line catalog (JSON; each line has an Id, LineCode, and English/Chinese names):\n{catalogJson}";
+    }
+
+    private static CategoryAiSuggestion BuildSuggestion(ModelAnswer answer, List<CatalogLine> catalog)
+    {
+        var suggestion = new CategoryAiSuggestion
+        {
+            ChineseName = string.IsNullOrWhiteSpace(answer.ChineseName) ? null : answer.ChineseName.Trim(),
+            EnglishName = string.IsNullOrWhiteSpace(answer.EnglishName) ? null : answer.EnglishName.Trim(),
+            Confidence = answer.Confidence,
+        };
+
+        // Re-validate the returned id against the catalog; drop a hallucinated id rather than returning it.
+        var line = catalog.FirstOrDefault(candidate => candidate.Id == answer.Form990LineId);
+        if (line is not null)
+        {
+            suggestion.Form990LineId = line.Id;
+            suggestion.Form990LineLabel = Label(line);
+        }
+
+        return suggestion;
+    }
+
+    /// <summary>Mirror the frontend dropdown label: "code — English / 中文" (or just "code — English").</summary>
+    private static string Label(CatalogLine line)
+        => string.IsNullOrWhiteSpace(line.NameZh)
+            ? $"{line.LineCode} — {line.NameEn}"
+            : $"{line.LineCode} — {line.NameEn} / {line.NameZh}";
+}

API/ROLAC.API/Services/Ai/ExpenseCategoryAiServiceFactory.cs

@@ -0,0 +1,30 @@
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>Selects the active category-AI provider per request from <c>ChurchProfile.AiProvider</c>.</summary>
+public interface IExpenseCategoryAiServiceFactory
+{
+    Task<IExpenseCategoryAiService> ResolveAsync(CancellationToken ct = default);
+}
+
+public sealed class ExpenseCategoryAiServiceFactory : IExpenseCategoryAiServiceFactory
+{
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ClaudeExpenseCategoryAiService _claude;
+    private readonly GeminiExpenseCategoryAiService _gemini;
+
+    public ExpenseCategoryAiServiceFactory(
+        IChurchAiConfigProvider config,
+        ClaudeExpenseCategoryAiService claude,
+        GeminiExpenseCategoryAiService gemini)
+    {
+        _config = config;
+        _claude = claude;
+        _gemini = gemini;
+    }
+
+    public async Task<IExpenseCategoryAiService> ResolveAsync(CancellationToken ct = default)
+    {
+        var cfg = await _config.GetAsync(ct);
+        return cfg.Provider.Equals("Gemini", StringComparison.OrdinalIgnoreCase) ? _gemini : _claude;
+    }
+}

API/ROLAC.API/Services/Ai/GeminiExpenseAiService.cs

@@ -0,0 +1,120 @@
+using System.Net.Http.Json;
+using System.Text.Json;
+using ROLAC.API.Data;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Translates and classifies an expense via the Google Gemini <c>generateContent</c> API, using
+/// Gemini's structured-output mode (<c>responseSchema</c>). The catalog, prompt, and id validation
+/// come from <see cref="ExpenseAiServiceBase"/>; this class only owns the Gemini HTTP call + parse.
+/// </summary>
+public sealed class GeminiExpenseAiService : ExpenseAiServiceBase
+{
+    private const string BaseUrl = "https://generativelanguage.googleapis.com/v1beta";
+
+    private readonly HttpClient _http;
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ILogger<GeminiExpenseAiService> _logger;
+
+    public GeminiExpenseAiService(
+        HttpClient http,
+        IChurchAiConfigProvider config,
+        AppDbContext db,
+        ILogger<GeminiExpenseAiService> logger)
+        : base(db)
+    {
+        _http = http;
+        _config = config;
+        _logger = logger;
+    }
+
+    protected override async Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct)
+    {
+        var cfg = await _config.GetAsync(ct);
+        if (string.IsNullOrWhiteSpace(cfg.GeminiApiKey))
+        {
+            _logger.LogWarning("Gemini API key is not configured; expense AI assist is disabled.");
+            return null;
+        }
+
+        try
+        {
+            var payload = new
+            {
+                contents = new[]
+                {
+                    new { parts = new[] { new { text = prompt } } },
+                },
+                generationConfig = new
+                {
+                    responseMimeType = "application/json",
+                    responseSchema = new
+                    {
+                        type = "object",
+                        properties = new
+                        {
+                            chineseDescription = new { type = "string" },
+                            englishDescription = new { type = "string" },
+                            groupId = new { type = "integer" },
+                            subCategoryId = new { type = "integer" },
+                            confidence = new { type = "number" },
+                        },
+                        required = new[] { "chineseDescription", "englishDescription", "groupId", "subCategoryId", "confidence" },
+                    },
+                },
+            };
+
+            var url = $"{BaseUrl}/models/{cfg.GeminiModel}:generateContent";
+            using var request = new HttpRequestMessage(HttpMethod.Post, url)
+            {
+                Content = JsonContent.Create(payload),
+            };
+            request.Headers.Add("X-goog-api-key", cfg.GeminiApiKey);
+
+            using var response = await _http.SendAsync(request, ct);
+            if (!response.IsSuccessStatusCode)
+            {
+                var body = await response.Content.ReadAsStringAsync(ct);
+                _logger.LogWarning("Gemini returned {Status}: {Body}", (int)response.StatusCode, body);
+                return null;
+            }
+
+            // Navigate candidates[0].content.parts[0].text — the model's JSON answer as a string.
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStreamAsync(ct));
+            var text = doc.RootElement
+                .GetProperty("candidates")[0]
+                .GetProperty("content")
+                .GetProperty("parts")[0]
+                .GetProperty("text")
+                .GetString();
+
+            if (string.IsNullOrWhiteSpace(text))
+            {
+                _logger.LogWarning("Gemini response contained no text part.");
+                return null;
+            }
+
+            var parsed = JsonSerializer.Deserialize<GeminiAnswer>(
+                text, new JsonSerializerOptions { PropertyNameCaseInsensitive = true });
+            if (parsed is null) return null;
+
+            return new ModelAnswer(parsed.EnglishDescription, parsed.ChineseDescription, parsed.GroupId, parsed.SubCategoryId, parsed.Confidence);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Gemini expense AI assist failed.");
+            return null;
+        }
+    }
+
+    /// <summary>Shape of Gemini's JSON answer (constrained by responseSchema).</summary>
+    private sealed class GeminiAnswer
+    {
+        public string? EnglishDescription { get; set; }
+        public string? ChineseDescription { get; set; }
+        public int     GroupId            { get; set; }
+        public int     SubCategoryId      { get; set; }
+        public double  Confidence         { get; set; }
+    }
+}

API/ROLAC.API/Services/Ai/GeminiExpenseCategoryAiService.cs

@@ -0,0 +1,119 @@
+using System.Net.Http.Json;
+using System.Text.Json;
+using ROLAC.API.Data;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// Refines, translates, and maps an expense category to a Form 990 line via the Google Gemini
+/// <c>generateContent</c> API, using Gemini's structured-output mode (<c>responseSchema</c>). The
+/// catalog, prompt, and id validation come from <see cref="ExpenseCategoryAiServiceBase"/>; this class
+/// only owns the Gemini HTTP call + parse.
+/// </summary>
+public sealed class GeminiExpenseCategoryAiService : ExpenseCategoryAiServiceBase
+{
+    private const string BaseUrl = "https://generativelanguage.googleapis.com/v1beta";
+
+    private readonly HttpClient _http;
+    private readonly IChurchAiConfigProvider _config;
+    private readonly ILogger<GeminiExpenseCategoryAiService> _logger;
+
+    public GeminiExpenseCategoryAiService(
+        HttpClient http,
+        IChurchAiConfigProvider config,
+        AppDbContext db,
+        ILogger<GeminiExpenseCategoryAiService> logger)
+        : base(db)
+    {
+        _http = http;
+        _config = config;
+        _logger = logger;
+    }
+
+    protected override async Task<ModelAnswer?> CallModelAsync(string prompt, CancellationToken ct)
+    {
+        var cfg = await _config.GetAsync(ct);
+        if (string.IsNullOrWhiteSpace(cfg.GeminiApiKey))
+        {
+            _logger.LogWarning("Gemini API key is not configured; category AI assist is disabled.");
+            return null;
+        }
+
+        try
+        {
+            var payload = new
+            {
+                contents = new[]
+                {
+                    new { parts = new[] { new { text = prompt } } },
+                },
+                generationConfig = new
+                {
+                    responseMimeType = "application/json",
+                    responseSchema = new
+                    {
+                        type = "object",
+                        properties = new
+                        {
+                            chineseName = new { type = "string" },
+                            englishName = new { type = "string" },
+                            form990LineId = new { type = "integer" },
+                            confidence = new { type = "number" },
+                        },
+                        required = new[] { "chineseName", "englishName", "form990LineId", "confidence" },
+                    },
+                },
+            };
+
+            var url = $"{BaseUrl}/models/{cfg.GeminiModel}:generateContent";
+            using var request = new HttpRequestMessage(HttpMethod.Post, url)
+            {
+                Content = JsonContent.Create(payload),
+            };
+            request.Headers.Add("X-goog-api-key", cfg.GeminiApiKey);
+
+            using var response = await _http.SendAsync(request, ct);
+            if (!response.IsSuccessStatusCode)
+            {
+                var body = await response.Content.ReadAsStringAsync(ct);
+                _logger.LogWarning("Gemini returned {Status}: {Body}", (int)response.StatusCode, body);
+                return null;
+            }
+
+            // Navigate candidates[0].content.parts[0].text — the model's JSON answer as a string.
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStreamAsync(ct));
+            var text = doc.RootElement
+                .GetProperty("candidates")[0]
+                .GetProperty("content")
+                .GetProperty("parts")[0]
+                .GetProperty("text")
+                .GetString();
+
+            if (string.IsNullOrWhiteSpace(text))
+            {
+                _logger.LogWarning("Gemini response contained no text part.");
+                return null;
+            }
+
+            var parsed = JsonSerializer.Deserialize<GeminiAnswer>(
+                text, new JsonSerializerOptions { PropertyNameCaseInsensitive = true });
+            if (parsed is null) return null;
+
+            return new ModelAnswer(parsed.ChineseName, parsed.EnglishName, parsed.Form990LineId, parsed.Confidence);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Gemini category AI assist failed.");
+            return null;
+        }
+    }
+
+    /// <summary>Shape of Gemini's JSON answer (constrained by responseSchema).</summary>
+    private sealed class GeminiAnswer
+    {
+        public string? ChineseName   { get; set; }
+        public string? EnglishName   { get; set; }
+        public int?    Form990LineId { get; set; }
+        public double  Confidence    { get; set; }
+    }
+}

API/ROLAC.API/Services/Ai/IExpenseAiService.cs

@@ -0,0 +1,14 @@
+using ROLAC.API.DTOs.Expense;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>AI assistance for expense entry: translate a description and suggest a category.</summary>
+public interface IExpenseAiService
+{
+    /// <summary>
+    /// Translate <paramref name="chineseText"/> to concise accounting English and suggest the best
+    /// major/sub category from the live catalog, using <paramref name="amount"/> as a hint.
+    /// Never throws on an upstream/AI failure — returns a suggestion with null fields instead.
+    /// </summary>
+    Task<ExpenseAiSuggestion> SuggestAsync(string chineseText, decimal amount, CancellationToken ct = default);
+}

API/ROLAC.API/Services/Ai/IExpenseCategoryAiService.cs

@@ -0,0 +1,17 @@
+using ROLAC.API.DTOs.Expense;
+
+namespace ROLAC.API.Services.Ai;
+
+/// <summary>
+/// AI assistance for defining an expense category (大項/小項): refine the Chinese name, translate it
+/// to English, and suggest the matching IRS Form 990 Part IX line.
+/// </summary>
+public interface IExpenseCategoryAiService
+{
+    /// <summary>
+    /// Refine the entered name, translate it to concise accounting English, and choose the best Form 990
+    /// line from the live catalog (biased by the group/sub context in <paramref name="request"/>).
+    /// Never throws on an upstream/AI failure — returns a suggestion with null fields instead.
+    /// </summary>
+    Task<CategoryAiSuggestion> SuggestAsync(ExpenseCategoryAiRequest request, CancellationToken ct = default);
+}

API/ROLAC.API/Services/ChurchProfileService.cs

@@ -18,7 +18,12 @@ public class ChurchProfileService : IChurchProfileService
             Id = p.Id, Name = p.Name, NameZh = p.NameZh, Phone = p.Phone, Email = p.Email,
             Website = p.Website, Address = p.Address, City = p.City, State = p.State,
             ZipCode = p.ZipCode, BankName = p.BankName, BankAccountNumber = p.BankAccountNumber,
-            BankRoutingNumber = p.BankRoutingNumber, NextCheckNumber = p.NextCheckNumber,
+            BankRoutingNumber = p.BankRoutingNumber, PayerEin = p.PayerEin, NextCheckNumber = p.NextCheckNumber,
+            AiProvider = p.AiProvider,
+            ClaudeModel = p.ClaudeModel,
+            ClaudeApiKeyMasked = Mask(p.ClaudeApiKey),
+            GeminiModel = p.GeminiModel,
+            GeminiApiKeyMasked = Mask(p.GeminiApiKey),
         };
     }
 
@@ -28,7 +33,13 @@ public class ChurchProfileService : IChurchProfileService
         p.Name = r.Name; p.NameZh = r.NameZh; p.Phone = r.Phone; p.Email = r.Email;
         p.Website = r.Website; p.Address = r.Address; p.City = r.City; p.State = r.State;
         p.ZipCode = r.ZipCode; p.BankName = r.BankName; p.BankAccountNumber = r.BankAccountNumber;
-        p.BankRoutingNumber = r.BankRoutingNumber; p.NextCheckNumber = r.NextCheckNumber;
+        p.BankRoutingNumber = r.BankRoutingNumber; p.PayerEin = r.PayerEin; p.NextCheckNumber = r.NextCheckNumber;
+        p.AiProvider  = string.IsNullOrWhiteSpace(r.AiProvider) ? "Claude" : r.AiProvider;
+        p.ClaudeModel = r.ClaudeModel;
+        p.GeminiModel = r.GeminiModel;
+        // Leave-unchanged semantics: only overwrite a stored key when a new value is supplied.
+        if (!string.IsNullOrWhiteSpace(r.ClaudeApiKey)) p.ClaudeApiKey = r.ClaudeApiKey;
+        if (!string.IsNullOrWhiteSpace(r.GeminiApiKey)) p.GeminiApiKey = r.GeminiApiKey;
         await _db.SaveChangesAsync();
     }
 
@@ -43,4 +54,12 @@ public class ChurchProfileService : IChurchProfileService
         }
         return p;
     }
+
+    /// <summary>Mask a stored secret for display: 6 bullets + last 4 chars; fully masked when ≤4 chars.</summary>
+    private static string Mask(string? key)
+    {
+        if (string.IsNullOrEmpty(key)) return "";
+        if (key.Length <= 4) return new string('•', key.Length);
+        return new string('•', 6) + key[^4..];
+    }
 }

API/ROLAC.API/Services/Disbursement/CheckPrintLayoutOptions.cs

@@ -0,0 +1,86 @@
+namespace ROLAC.API.Services.Disbursement;
+
+/// <summary>
+/// Field coordinates (in inches) for printing onto pre-printed three-stub check stock.
+/// Every position is bound from the "CheckPrint:Layout" section of appsettings.json so alignment
+/// can be tuned and reloaded without recompiling. Positions are expressed as an X (absolute from the
+/// page's left edge) plus a Y offset within the field's stub; the per-stub origins below place the
+/// three stacked regions (check + two identical receipt copies) down the 8.5"x11" page.
+/// </summary>
+public sealed class CheckPrintLayoutOptions
+{
+    // Calibration nudge (inches): a TextBox renders its text inset down-and-right from the box
+    // origin by a fixed internal margin + line leading, so configured X/Y don't match the ink.
+    // These values are subtracted from every position so configured X/Y == actual printed position.
+    // To recalibrate: set both to 0, print, measure how far the ink sits past a known X/Y, and put
+    // those differences here (defaults are the measured inset for this stock).
+    public float TextInsetX { get; set; } = 0.13f;
+    public float TextInsetY { get; set; } = 0.15f;
+
+    // Stub origins — top edge of each region, inches from the top of the page.
+    public float CheckOriginY    { get; set; } = 0f;
+    public float Receipt1OriginY { get; set; } = 3.67f;
+    public float Receipt2OriginY { get; set; } = 7.33f;
+
+    // Check stub fields (offset within the check stub).
+    public FieldPos Payee         { get; set; } = new() { X = 1.25f, OffsetY = 1.75f, FontSize = 11, Bold = true };
+    public FieldPos AmountNumeric { get; set; } = new() { X = 6.50f, OffsetY = 1.75f, FontSize = 11, Bold = true };
+    public FieldPos AmountWords   { get; set; } = new() { X = 0.60f, OffsetY = 2.20f, FontSize = 10 };
+    public FieldPos Memo          { get; set; } = new() { X = 0.60f, OffsetY = 2.90f, FontSize = 9  };
+    public FieldPos CheckDate     { get; set; } = new() { X = 6.50f, OffsetY = 1.25f, FontSize = 10 };
+
+    // Receipt stub fields (offset within a receipt stub — shared by both identical copies).
+    public FieldPos ReceiptPayee  { get; set; } = new() { X = 1.00f, OffsetY = 0.30f, FontSize = 10, Bold = true };
+    public FieldPos ReceiptAmount { get; set; } = new() { X = 6.50f, OffsetY = 0.30f, FontSize = 10, Bold = true };
+    public FieldPos ReceiptMemo   { get; set; } = new() { X = 1.00f, OffsetY = 0.60f, FontSize = 9  };
+    public FieldPos ReceiptDate   { get; set; } = new() { X = 6.50f, OffsetY = 0.60f, FontSize = 9  };
+
+    // Voucher detail grid (offsets within a receipt stub).
+    public VoucherGridOptions Grid { get; set; } = new();
+}
+
+/// <summary>One printable field: where it sits and how it renders.</summary>
+public sealed class FieldPos
+{
+    /// <summary>Absolute X from the page's left edge, in inches.</summary>
+    public float X { get; set; }
+
+    /// <summary>Y offset within the field's stub, in inches (added to the stub origin).</summary>
+    public float OffsetY { get; set; }
+
+    public float FontSize { get; set; } = 10;
+    public bool  Bold { get; set; }
+}
+
+/// <summary>
+/// Two-column voucher detail grid on each receipt stub: 6 rows per column, 12 expense lines max,
+/// filled column-major (lines 1-6 left, 7-12 right). All offsets are within the receipt stub.
+/// </summary>
+public sealed class VoucherGridOptions
+{
+    /// <summary>Left edge of the left column block, in inches from the page's left edge.</summary>
+    public float OriginX     { get; set; } = 0.60f;
+
+    /// <summary>Y offset (within the stub) of the first data row.</summary>
+    public float OffsetY     { get; set; } = 1.10f;
+
+    public float RowHeight   { get; set; } = 0.22f;
+
+    /// <summary>Horizontal gap between the left and right column blocks, in inches.</summary>
+    public float ColumnGap   { get; set; } = 0.30f;
+
+    public float DateWidth   { get; set; } = 0.85f;
+    public float DescWidth   { get; set; } = 2.10f;
+    public float AmountWidth { get; set; } = 0.80f;
+
+    /// <summary>Draw our own Date/Description/Amount headers. Set false if the stock pre-prints them.</summary>
+    public bool  ShowGridHeaders { get; set; } = true;
+
+    /// <summary>Y offset (within the stub) of the header row.</summary>
+    public float HeaderOffsetY   { get; set; } = 0.88f;
+
+    /// <summary>Y offset (within the stub) of the "...and N more lines" overflow hint.</summary>
+    public float OverflowOffsetY { get; set; } = 2.55f;
+
+    public float FontSize    { get; set; } = 8.5f;
+}

API/ROLAC.API/Services/Disbursement/CheckPrintService.cs

@@ -1,17 +1,28 @@
+using System.Drawing;
 using System.Globalization;
 using DevExpress.Office;
 using DevExpress.XtraRichEdit;
 using DevExpress.XtraRichEdit.API.Native;
+using Microsoft.Extensions.Options;
 
 namespace ROLAC.API.Services.Disbursement;
 
 /// <summary>
-/// Renders a check on 8.5"x11" stock using the DevExpress Office (RichEdit) API:
+/// Renders a check onto pre-printed 8.5"x11" three-stub stock using the DevExpress Office
-/// a check block on top followed by two identical ledger detail stubs. The layout is
+/// (RichEdit) API. Fields are placed as absolutely-positioned floating TextBoxes so they align to
-/// built programmatically (no external .docx template) and exported to PDF.
+/// the boxes printed on the stock; every coordinate comes from <see cref="CheckPrintLayoutOptions"/>
+/// (bound from "CheckPrint:Layout" in appsettings.json) so alignment can be tuned without recompiling.
+/// The page is one check stub on top followed by two identical receipt copies.
 /// </summary>
 public class CheckPrintService : ICheckPrintService
 {
+    private readonly CheckPrintLayoutOptions _layout;
+
+    public CheckPrintService(IOptions<CheckPrintLayoutOptions> layout)
+    {
+        _layout = layout.Value;
+    }
+
     public Task<Stream> RenderPdfAsync(CheckPrintModel model)
     {
         using var server = new RichEditDocumentServer();
@@ -26,9 +37,13 @@ public class CheckPrintService : ICheckPrintService
             section.Margins.Left = section.Margins.Right = 0.6f;
             section.Margins.Top = section.Margins.Bottom = 0.5f;
 
-            BuildCheckBlock(doc, model);
+            // Floating TextBoxes must anchor to a paragraph; everything is positioned relative to
-            BuildStub(doc, model, "PAYMENT ADVICE — DETAIL");
+            // the page, so a single empty anchor paragraph at the document start is enough.
-            BuildStub(doc, model, "PAYMENT ADVICE — RECORD COPY");
+            var anchor = doc.Paragraphs[0];
+
+            BuildCheckStub(doc, anchor, model);
+            BuildReceiptStub(doc, anchor, model, _layout.Receipt1OriginY);
+            BuildReceiptStub(doc, anchor, model, _layout.Receipt2OriginY);
         }
         finally
         {
@@ -41,6 +56,125 @@ public class CheckPrintService : ICheckPrintService
         return Task.FromResult<Stream>(ms);
     }
 
+    // ── check page builders (absolute positioning) ─────────────────────────────
+
+    private void BuildCheckStub(Document doc, Paragraph anchor, CheckPrintModel model)
+    {
+        var check = model.Check;
+        var originY = _layout.CheckOriginY;
+
+        PlaceField(doc, anchor, _layout.Payee, originY, 4.5f, check.PayeeName);
+        PlaceField(doc, anchor, _layout.AmountNumeric, originY, 1.6f, FormatCurrency(check.Amount,13), rightAlign: false);
+        PlaceField(doc, anchor, _layout.AmountWords, originY, 6.0f, model.AmountInWords);
+        PlaceField(doc, anchor, _layout.CheckDate, originY, 1.6f, check.CheckDate.ToString("MM/dd/yyyy"));
+        if (!string.IsNullOrWhiteSpace(check.Memo))
+            PlaceField(doc, anchor, _layout.Memo, originY, 4.5f, check.Memo);
+    }
+
+    private void BuildReceiptStub(Document doc, Paragraph anchor, CheckPrintModel model, float originY)
+    {
+        var check = model.Check;
+
+        PlaceField(doc, anchor, _layout.ReceiptPayee, originY, 4.5f, "Pay To The Order Of: " + check.PayeeName);
+        PlaceField(doc, anchor, _layout.ReceiptAmount, originY, 1.6f, "Amount: " + FormatCurrency(check.Amount), rightAlign: true);
+        PlaceField(doc, anchor, _layout.ReceiptDate, originY, 1.6f, check.CheckDate.ToString("MM/dd/yyyy"));
+        if (!string.IsNullOrWhiteSpace(check.Memo))
+            PlaceField(doc, anchor, _layout.ReceiptMemo, originY, 4.5f, check.Memo);
+
+        BuildVoucherGrid(doc, anchor, model, originY);
+    }
+
+    /// <summary>
+    /// Two-column voucher detail grid: up to 12 expense lines (6 per column), filled column-major.
+    /// Beyond 12 lines, prints the first 12 plus an overflow hint so the receipt total stays honest.
+    /// </summary>
+    private void BuildVoucherGrid(Document doc, Paragraph anchor, CheckPrintModel model, float originY)
+    {
+        var grid = _layout.Grid;
+        var blockWidth = grid.DateWidth + grid.DescWidth + grid.AmountWidth;
+        const int rowsPerColumn = 6;
+        const int maxLines = rowsPerColumn * 2;
+
+        float ColumnX(int column) => grid.OriginX + column * (blockWidth + grid.ColumnGap);
+
+        void PlaceRow(float x, float y, string date, string description, string amount, bool bold)
+        {
+            PlaceText(doc, anchor, x, y, grid.DateWidth, date, grid.FontSize, bold, rightAlign: false);
+            PlaceText(doc, anchor, x + grid.DateWidth, y, grid.DescWidth, description, grid.FontSize, bold, rightAlign: false);
+            PlaceText(doc, anchor, x + grid.DateWidth + grid.DescWidth, y, grid.AmountWidth, amount, grid.FontSize, bold, rightAlign: true);
+        }
+
+        if (grid.ShowGridHeaders)
+        {
+            var headerY = originY + grid.HeaderOffsetY;
+            for (var column = 0; column < 2; column++)
+                PlaceRow(ColumnX(column), headerY, "Date", "Description", "Amount", bold: true);
+        }
+
+        var printed = Math.Min(model.Lines.Count, maxLines);
+        for (var i = 0; i < printed; i++)
+        {
+            var line = model.Lines[i];
+            var column = i < rowsPerColumn ? 0 : 1;
+            var row = i % rowsPerColumn;
+            var y = originY + grid.OffsetY + row * grid.RowHeight;
+            var date = line.Expense?.ExpenseDate.ToString("MM/dd/yyyy") ?? "";
+            PlaceRow(ColumnX(column), y, date, line.Description, FormatCurrency(line.Amount), bold: false);
+        }
+
+        if (model.Lines.Count > maxLines)
+        {
+            var remaining = model.Lines.Count - maxLines;
+            var remainingTotal = model.Lines.Skip(maxLines).Sum(line => line.Amount);
+            var hint = $"…and {remaining} more line(s) ({FormatCurrency(remainingTotal)})";
+            PlaceText(doc, anchor, grid.OriginX, originY + grid.OverflowOffsetY,
+                blockWidth * 2 + grid.ColumnGap, hint, grid.FontSize, bold: false, rightAlign: false);
+        }
+    }
+
+    /// <summary>Places one configured field's value at its stub-relative position.</summary>
+    private void PlaceField(Document doc, Paragraph anchor, FieldPos field, float stubOriginY,
+        float width, string text, bool rightAlign = false)
+    {
+        PlaceText(doc, anchor, field.X, stubOriginY + field.OffsetY, width, text,
+            field.FontSize, field.Bold, rightAlign);
+    }
+
+    /// <summary>
+    /// Inserts a borderless, fill-less floating TextBox positioned absolutely relative to the page
+    /// (X from the left edge, Y from the top edge) and writes <paramref name="text"/> into it.
+    /// </summary>
+    private void PlaceText(Document doc, Paragraph anchor, float x, float y, float width,
+        string text, float fontSize, bool bold, bool rightAlign)
+    {
+        var shape = doc.Shapes.InsertTextBox(anchor.Range.Start);
+        shape.HorizontalAlignment = ShapeHorizontalAlignment.None;
+        shape.VerticalAlignment = ShapeVerticalAlignment.None;
+        shape.RelativeHorizontalPosition = ShapeRelativeHorizontalPosition.Page;
+        shape.RelativeVerticalPosition = ShapeRelativeVerticalPosition.Page;
+        // Pull the box up-and-left by the calibration inset so the text inside lands exactly on the
+        // configured (x, y) rather than down-and-right of it.
+        shape.Offset = new PointF(x - _layout.TextInsetX, y - _layout.TextInsetY);
+        shape.Size = new SizeF(width, Math.Max(0.2f, fontSize / 72f + 0.08f));
+        shape.Fill.SetNoFill();
+        shape.Line.Fill.SetNoFill();
+
+        var body = shape.ShapeFormat.TextBox.Document;
+        var range = body.InsertText(body.Range.Start, text);
+
+        var characters = body.BeginUpdateCharacters(range);
+        characters.FontSize = fontSize;
+        characters.Bold = bold;
+        body.EndUpdateCharacters(characters);
+
+        if (rightAlign)
+        {
+            var paragraphs = body.BeginUpdateParagraphs(range);
+            paragraphs.Alignment = ParagraphAlignment.Right;
+            body.EndUpdateParagraphs(paragraphs);
+        }
+    }
+
     public Task<Stream> RenderReceiptPdfAsync(CheckPrintModel model)
     {
         using var server = new RichEditDocumentServer();
@@ -131,110 +265,15 @@ public class CheckPrintService : ICheckPrintService
 
     private static string Encode(string? text) => System.Net.WebUtility.HtmlEncode(text ?? "");
 
-    private static void BuildCheckBlock(Document doc, CheckPrintModel m)
-    {
-        var issuer = m.Issuer;
-        var check  = m.Check;
-
-        AppendLine(doc, issuer.Name, bold: true, size: 13);
-        var issuerAddr = JoinAddress(issuer.Address, issuer.City, issuer.State, issuer.ZipCode);
-        if (!string.IsNullOrWhiteSpace(issuerAddr)) AppendLine(doc, issuerAddr, size: 9);
-        if (!string.IsNullOrWhiteSpace(issuer.BankName)) AppendLine(doc, issuer.BankName, size: 9);
-
-        AppendLine(doc, "");
-        AppendLine(doc, $"Check No: {check.CheckNumber}        Date: {check.CheckDate:MM/dd/yyyy}", bold: true, size: 10);
-        AppendLine(doc, "");
-
-        AppendLine(doc, $"PAY TO THE ORDER OF:  {check.PayeeName}", bold: true, size: 11);
-        var payeeAddr = JoinAddress(check.PayeeAddress, check.PayeeCity, check.PayeeState, check.PayeeZip);
-        if (!string.IsNullOrWhiteSpace(payeeAddr)) AppendLine(doc, payeeAddr, size: 9);
-
-        AppendLine(doc, "");
-        AppendLine(doc, $"AMOUNT:  {FormatCurrency(check.Amount)}", bold: true, size: 12);
-        AppendLine(doc, m.AmountInWords, size: 10);
-
-        if (!string.IsNullOrWhiteSpace(check.Memo)) { AppendLine(doc, ""); AppendLine(doc, $"Memo: {check.Memo}", size: 9); }
-
-        AppendLine(doc, "");
-        AppendLine(doc, "____________________________________", size: 10);
-        AppendLine(doc, "Authorized Signature", size: 8);
-        AppendSeparator(doc);
-    }
-
-    private static void BuildStub(Document doc, CheckPrintModel m, string title)
-    {
-        var check = m.Check;
-        AppendLine(doc, title, bold: true, size: 10);
-        AppendLine(doc, $"Check No: {check.CheckNumber}    Date: {check.CheckDate:MM/dd/yyyy}    Payee: {check.PayeeName}", size: 9);
-        AppendLine(doc, "");
-
-        var rows = m.Lines.Count + 2; // header + lines + total
-        var table = doc.Tables.Create(doc.Range.End, rows, 3, AutoFitBehaviorType.AutoFitToWindow);
-        table.Borders.InsideHorizontalBorder.LineStyle = TableBorderLineStyle.Single;
-        table.Borders.Top.LineStyle = table.Borders.Bottom.LineStyle = TableBorderLineStyle.Single;
-
-        SetCell(doc, table[0, 0], "Date", bold: true);
-        SetCell(doc, table[0, 1], "Description", bold: true);
-        SetCell(doc, table[0, 2], "Amount", bold: true, right: true);
-
-        for (var i = 0; i < m.Lines.Count; i++)
-        {
-            var line = m.Lines[i];
-            var r = i + 1;
-            // CheckLine snapshots description; date comes from the source expense if loaded.
-            var date = line.Expense?.ExpenseDate.ToString("MM/dd/yyyy") ?? "";
-            SetCell(doc, table[r, 0], date);
-            SetCell(doc, table[r, 1], line.Description);
-            SetCell(doc, table[r, 2], FormatCurrency(line.Amount), right: true);
-        }
-
-        var totalRow = rows - 1;
-        SetCell(doc, table[totalRow, 0], "");
-        SetCell(doc, table[totalRow, 1], "TOTAL", bold: true, right: true);
-        SetCell(doc, table[totalRow, 2], FormatCurrency(check.Amount), bold: true, right: true);
-
-        AppendLine(doc, "");
-        if (check.ReceiptSignedAt is { } signedAt)
-            AppendLine(doc, $"Received by: {check.ReceiptSignedName}    on {signedAt:MM/dd/yyyy HH:mm}", size: 9);
-        AppendSeparator(doc);
-    }
-
     // ── low-level helpers ──────────────────────────────────────────────────────
-
+    private static string FormatCurrency(decimal amount, int paddingAstric = 0)
-    private static void AppendLine(Document doc, string text, bool bold = false, float size = 10)
     {
-        var range = doc.AppendText(text + "\r\n");
+        var c = (CultureInfo)CultureInfo.GetCultureInfo("en-US").Clone();
-        var cp = doc.BeginUpdateCharacters(range);
+        c.NumberFormat.CurrencySymbol = "";
-        cp.Bold = bold;
+        string formatedAmount = amount.ToString("#,##0.00", CultureInfo.GetCultureInfo("en-US"));
-        cp.FontSize = size;
+        return paddingAstric > 0 ? formatedAmount.PadLeft(paddingAstric, '*') : formatedAmount;
-        doc.EndUpdateCharacters(cp);
     }
 
-    private static void AppendSeparator(Document doc)
-    {
-        AppendLine(doc, "");
-        AppendLine(doc, "------------------------------------------------------------------------------------------", size: 8);
-        AppendLine(doc, "");
-    }
-
-    private static void SetCell(Document doc, TableCell cell, string text, bool bold = false, bool right = false)
-    {
-        var range = doc.InsertText(cell.ContentRange.Start, text);
-        var cp = doc.BeginUpdateCharacters(range);
-        cp.Bold = bold;
-        cp.FontSize = 9;
-        doc.EndUpdateCharacters(cp);
-        if (right)
-        {
-            var pp = doc.BeginUpdateParagraphs(range);
-            pp.Alignment = ParagraphAlignment.Right;
-            doc.EndUpdateParagraphs(pp);
-        }
-    }
-
-    private static string FormatCurrency(decimal amount) =>
-        amount.ToString("C2", CultureInfo.GetCultureInfo("en-US"));
-
     private static string JoinAddress(string? addr, string? city, string? state, string? zip)
     {
         var cityLine = string.Join(", ",

API/ROLAC.API/Services/DisbursementService.cs

@@ -40,6 +40,19 @@ public class DisbursementService : IDisbursementService
         var memberIds = rows.Where(r => r.MemberId != null).Select(r => r.MemberId!.Value).ToHashSet();
         var members = await _db.Members.AsNoTracking().Where(m => memberIds.Contains(m.Id)).ToDictionaryAsync(m => m.Id);
 
+        // Category label per expense: the single line's category, or "Multiple" when it spans several.
+        var expenseIds = rows.Select(r => r.Id).ToList();
+        var lineGroups = await _db.ExpenseLines.AsNoTracking()
+            .Where(l => expenseIds.Contains(l.ExpenseId))
+            .OrderBy(l => l.Id)
+            .Select(l => new { l.ExpenseId, l.CategoryGroupId })
+            .ToListAsync();
+        var categoryByExpense = lineGroups.GroupBy(l => l.ExpenseId).ToDictionary(
+            g => g.Key,
+            g => g.Select(l => l.CategoryGroupId).Distinct().Count() > 1
+                ? "Multiple / 多類別"
+                : grpNames.GetValueOrDefault(g.First().CategoryGroupId, ""));
+
         var groups = new Dictionary<string, PayeeGroupDto>();
         foreach (var e in rows)
         {
@@ -77,7 +90,7 @@ public class DisbursementService : IDisbursementService
                 ExpenseId = e.Id, ExpenseDate = e.ExpenseDate.ToString("yyyy-MM-dd"),
                 Description = e.Description, Amount = e.Amount,
                 MinistryName = minNames.GetValueOrDefault(e.MinistryId, ""),
-                CategoryName = grpNames.GetValueOrDefault(e.CategoryGroupId, ""),
+                CategoryName = categoryByExpense.GetValueOrDefault(e.Id, ""),
             });
             g.TotalAmount += e.Amount;
         }

API/ROLAC.API/Services/ExpenseCategoryService.cs

@@ -25,25 +25,32 @@ public class ExpenseCategoryService : IExpenseCategoryService
         var lineCodes = await _db.Form990ExpenseLines.AsNoTracking()
             .ToDictionaryAsync(l => l.Id, l => l.LineCode);
 
+        var boxCodes = await _db.Form1099Boxes.AsNoTracking()
+            .ToDictionaryAsync(b => b.Id, b => b.BoxCode);
+
         return groups.Select(g => new ExpenseCategoryGroupDto
         {
             Id = g.Id, Name_en = g.Name_en, Name_zh = g.Name_zh,
             SortOrder = g.SortOrder, IsActive = g.IsActive,
             Form990LineId   = g.Form990LineId,
             Form990LineCode = g.Form990LineId.HasValue ? lineCodes.GetValueOrDefault(g.Form990LineId.Value) : null,
+            Form1099BoxId   = g.Form1099BoxId,
+            Form1099BoxCode = g.Form1099BoxId.HasValue ? boxCodes.GetValueOrDefault(g.Form1099BoxId.Value) : null,
             SubCategories = subs.Where(s => s.GroupId == g.Id).Select(s => new ExpenseSubCategoryDto
             {
                 Id = s.Id, GroupId = s.GroupId, Name_en = s.Name_en, Name_zh = s.Name_zh,
                 SortOrder = s.SortOrder, IsActive = s.IsActive,
                 Form990LineId   = s.Form990LineId,
                 Form990LineCode = s.Form990LineId.HasValue ? lineCodes.GetValueOrDefault(s.Form990LineId.Value) : null,
+                Form1099BoxId   = s.Form1099BoxId,
+                Form1099BoxCode = s.Form1099BoxId.HasValue ? boxCodes.GetValueOrDefault(s.Form1099BoxId.Value) : null,
             }).ToList(),
         }).ToList();
     }
 
     public async Task<int> CreateGroupAsync(CreateExpenseGroupRequest r)
     {
-        var g = new ExpenseCategoryGroup { Name_en = r.Name_en, Name_zh = r.Name_zh, SortOrder = r.SortOrder, IsActive = true, Form990LineId = r.Form990LineId };
+        var g = new ExpenseCategoryGroup { Name_en = r.Name_en, Name_zh = r.Name_zh, SortOrder = r.SortOrder, IsActive = true, Form990LineId = r.Form990LineId, Form1099BoxId = r.Form1099BoxId };
         _db.ExpenseCategoryGroups.Add(g);
         await _db.SaveChangesAsync();
         return g.Id;
@@ -53,7 +60,7 @@ public class ExpenseCategoryService : IExpenseCategoryService
     {
         var g = await _db.ExpenseCategoryGroups.FindAsync(id)
             ?? throw new KeyNotFoundException($"ExpenseCategoryGroup {id} not found.");
-        g.Name_en = r.Name_en; g.Name_zh = r.Name_zh; g.SortOrder = r.SortOrder; g.IsActive = r.IsActive; g.Form990LineId = r.Form990LineId;
+        g.Name_en = r.Name_en; g.Name_zh = r.Name_zh; g.SortOrder = r.SortOrder; g.IsActive = r.IsActive; g.Form990LineId = r.Form990LineId; g.Form1099BoxId = r.Form1099BoxId;
         await _db.SaveChangesAsync();
     }
 
@@ -69,7 +76,7 @@ public class ExpenseCategoryService : IExpenseCategoryService
     {
         var exists = await _db.ExpenseCategoryGroups.AnyAsync(g => g.Id == r.GroupId);
         if (!exists) throw new KeyNotFoundException($"ExpenseCategoryGroup {r.GroupId} not found.");
-        var s = new ExpenseSubCategory { GroupId = r.GroupId, Name_en = r.Name_en, Name_zh = r.Name_zh, SortOrder = r.SortOrder, IsActive = true, Form990LineId = r.Form990LineId };
+        var s = new ExpenseSubCategory { GroupId = r.GroupId, Name_en = r.Name_en, Name_zh = r.Name_zh, SortOrder = r.SortOrder, IsActive = true, Form990LineId = r.Form990LineId, Form1099BoxId = r.Form1099BoxId };
         _db.ExpenseSubCategories.Add(s);
         await _db.SaveChangesAsync();
         return s.Id;
@@ -79,7 +86,7 @@ public class ExpenseCategoryService : IExpenseCategoryService
     {
         var s = await _db.ExpenseSubCategories.FindAsync(id)
             ?? throw new KeyNotFoundException($"ExpenseSubCategory {id} not found.");
-        s.GroupId = r.GroupId; s.Name_en = r.Name_en; s.Name_zh = r.Name_zh; s.SortOrder = r.SortOrder; s.IsActive = r.IsActive; s.Form990LineId = r.Form990LineId;
+        s.GroupId = r.GroupId; s.Name_en = r.Name_en; s.Name_zh = r.Name_zh; s.SortOrder = r.SortOrder; s.IsActive = r.IsActive; s.Form990LineId = r.Form990LineId; s.Form1099BoxId = r.Form1099BoxId;
         await _db.SaveChangesAsync();
     }
 

API/ROLAC.API/Services/ExpenseService.cs

@@ -35,8 +35,9 @@ public class ExpenseService : IExpenseService
     {
         var query = _db.Expenses.AsNoTracking().AsQueryable();
         if (ministryId.HasValue)      query = query.Where(e => e.MinistryId == ministryId.Value);
-        if (categoryGroupId.HasValue) query = query.Where(e => e.CategoryGroupId == categoryGroupId.Value);
+        // Category filters now match against any line of the expense.
-        if (subCategoryId.HasValue)   query = query.Where(e => e.SubCategoryId == subCategoryId.Value);
+        if (categoryGroupId.HasValue) query = query.Where(e => e.Lines.Any(l => l.CategoryGroupId == categoryGroupId.Value));
+        if (subCategoryId.HasValue)   query = query.Where(e => e.Lines.Any(l => l.SubCategoryId == subCategoryId.Value));
         // `statuses` (comma-separated) takes precedence over single `status`; lets the dashboard
         // request the Paid+Approved set in one call.
         if (!string.IsNullOrWhiteSpace(statuses))
@@ -81,60 +82,173 @@ public class ExpenseService : IExpenseService
 
         var minNames = await _db.Ministries.AsNoTracking().ToDictionaryAsync(m => m.Id, m => $"{m.Name_en} / {m.Name_zh}");
         var grpNames = await _db.ExpenseCategoryGroups.AsNoTracking().ToDictionaryAsync(g => g.Id, g => $"{g.Name_en} / {g.Name_zh}");
-        var subNames = await _db.ExpenseSubCategories.AsNoTracking().ToDictionaryAsync(s => s.Id, s => $"{s.Name_en} / {s.Name_zh}");
         var memberIds = rows.Where(r => r.MemberId != null).Select(r => r.MemberId!.Value).ToHashSet();
-        var memNames = await _db.Members.AsNoTracking().Where(m => memberIds.Contains(m.Id))
+        var memberNames = await _db.Members.AsNoTracking().Where(m => memberIds.Contains(m.Id))
-            .ToDictionaryAsync(m => m.Id, m => $"{m.FirstName_en} {m.LastName_en}");
+            .Select(m => new { m.Id, m.FirstName_en, m.LastName_en, m.NickName })
+            .ToDictionaryAsync(
+                m => m.Id,
+                m => new MemberPayeeName($"{m.FirstName_en} {m.LastName_en}",
+                                         BuildNickPayeeName(m.NickName, m.FirstName_en, m.LastName_en)));
+        var reviewerNames = await ResolveUserNamesAsync(rows.Select(r => r.ReviewedBy));
 
-        var items = rows.Select(e => new ExpenseListItemDto
+        // Line count + first line's category, per expense on this page.
+        var expenseIds = rows.Select(r => r.Id).ToList();
+        var lineRows = await _db.ExpenseLines.AsNoTracking()
+            .Where(l => expenseIds.Contains(l.ExpenseId))
+            .OrderBy(l => l.Id)
+            .Select(l => new { l.ExpenseId, l.CategoryGroupId })
+            .ToListAsync();
+        var linesByExpense = lineRows.GroupBy(l => l.ExpenseId)
+            .ToDictionary(g => g.Key, g => g.ToList());
+
+        var items = rows.Select(e =>
+        {
+            linesByExpense.TryGetValue(e.Id, out var ls);
+            var firstGroupId = ls is { Count: > 0 } ? ls[0].CategoryGroupId : 0;
+            return new ExpenseListItemDto
             {
                 Id = e.Id, Type = e.Type, Status = e.Status, Amount = e.Amount, Description = e.Description,
                 MinistryId = e.MinistryId, MinistryName = minNames.GetValueOrDefault(e.MinistryId, ""),
-            CategoryGroupId = e.CategoryGroupId, CategoryGroupName = grpNames.GetValueOrDefault(e.CategoryGroupId, ""),
+                LineCount = ls?.Count ?? 0,
-            SubCategoryId = e.SubCategoryId, SubCategoryName = subNames.GetValueOrDefault(e.SubCategoryId, ""),
+                PrimaryCategoryName = grpNames.GetValueOrDefault(firstGroupId, ""),
                 VendorName = e.VendorName, MemberId = e.MemberId,
-            MemberName = e.MemberId != null ? memNames.GetValueOrDefault(e.MemberId.Value) : null,
+                MemberName = e.MemberId != null ? memberNames.GetValueOrDefault(e.MemberId.Value)?.Legal : null,
+                MemberNickName = e.MemberId != null ? memberNames.GetValueOrDefault(e.MemberId.Value)?.Nick : null,
                 ExpenseDate = e.ExpenseDate.ToString("yyyy-MM-dd"),
                 HasReceipt = e.ReceiptBlobPath != null,
                 CheckNumber = e.CheckNumber,
-            FunctionalClass = e.FunctionalClass,
+                ReviewedByName = e.ReviewedBy != null ? reviewerNames.GetValueOrDefault(e.ReviewedBy) : null,
+                ReviewedAt = e.ReviewedAt,
+                ReviewNotes = e.ReviewNotes,
+                PayeeId = e.PayeeId,
+            };
         }).ToList();
 
         return new PagedResult<ExpenseListItemDto> { Items = items, TotalCount = total, Page = page, PageSize = pageSize };
     }
 
+    // Resolve actor user ids (AppUser.Id, stored in ReviewedBy/SubmittedBy/PaidBy) to a display name:
+    // the linked Member's full name when present, otherwise the account email.
+    private async Task<Dictionary<string, string>> ResolveUserNamesAsync(IEnumerable<string?> userIds)
+    {
+        var ids = userIds.Where(id => !string.IsNullOrEmpty(id)).Select(id => id!).Distinct().ToList();
+        if (ids.Count == 0) return new Dictionary<string, string>();
+
+        var users = await _db.Users.AsNoTracking()
+            .Where(u => ids.Contains(u.Id))
+            .Select(u => new { u.Id, u.Email, u.MemberId })
+            .ToListAsync();
+
+        var memberIds = users.Where(u => u.MemberId != null).Select(u => u.MemberId!.Value).ToHashSet();
+        var memberNames = await _db.Members.AsNoTracking()
+            .Where(m => memberIds.Contains(m.Id))
+            .ToDictionaryAsync(m => m.Id, m => $"{m.FirstName_en} {m.LastName_en}".Trim());
+
+        return users.ToDictionary(
+            u => u.Id,
+            u => u.MemberId != null && memberNames.TryGetValue(u.MemberId.Value, out var name) && name.Length > 0
+                ? name
+                : (u.Email ?? u.Id));
+    }
+
+    // Member payee names carried to the frontend: the legal name (printed on the check) and an
+    // optional friendly "NickName LastName" line shown above it.
+    private sealed record MemberPayeeName(string Legal, string? Nick);
+
+    // Build the friendly "NickName LastName" payee line, or null when the member has no distinct
+    // nickname (mirrors the frontend memberDisplayName rule: a nickname equal to the first name is not shown).
+    private static string? BuildNickPayeeName(string? nickName, string firstNameEn, string lastNameEn)
+    {
+        bool hasDistinctNickName = !string.IsNullOrWhiteSpace(nickName) && nickName != firstNameEn;
+        if (!hasDistinctNickName)
+        {
+            return null;
+        }
+        return $"{nickName} {lastNameEn}";
+    }
+
     public async Task<ExpenseDto?> GetByIdAsync(int id)
     {
         var e = await _db.Expenses.AsNoTracking().FirstOrDefaultAsync(x => x.Id == id);
         if (e is null) return null;
         var minName = await _db.Ministries.Where(m => m.Id == e.MinistryId).Select(m => m.Name_en).FirstOrDefaultAsync() ?? "";
-        var grpName = await _db.ExpenseCategoryGroups.Where(g => g.Id == e.CategoryGroupId).Select(g => g.Name_en).FirstOrDefaultAsync() ?? "";
+        string? memberName     = null;
-        var subName = await _db.ExpenseSubCategories.Where(s => s.Id == e.SubCategoryId).Select(s => s.Name_en).FirstOrDefaultAsync() ?? "";
+        string? memberNickName = null;
-        string? memName = e.MemberId != null
+        if (e.MemberId != null)
-            ? await _db.Members.Where(m => m.Id == e.MemberId).Select(m => m.FirstName_en + " " + m.LastName_en).FirstOrDefaultAsync()
+        {
+            var member = await _db.Members.AsNoTracking()
+                .Where(m => m.Id == e.MemberId)
+                .Select(m => new { m.FirstName_en, m.LastName_en, m.NickName })
+                .FirstOrDefaultAsync();
+            if (member != null)
+            {
+                memberName     = $"{member.FirstName_en} {member.LastName_en}";
+                memberNickName = BuildNickPayeeName(member.NickName, member.FirstName_en, member.LastName_en);
+            }
+        }
+
+        var reviewerName = e.ReviewedBy != null
+            ? (await ResolveUserNamesAsync(new[] { e.ReviewedBy })).GetValueOrDefault(e.ReviewedBy)
             : null;
+
+        var lines = await _db.ExpenseLines.AsNoTracking().Where(l => l.ExpenseId == id).OrderBy(l => l.Id).ToListAsync();
+        var grpNames = await _db.ExpenseCategoryGroups.AsNoTracking().ToDictionaryAsync(g => g.Id, g => g.Name_en);
+        var subNames = await _db.ExpenseSubCategories.AsNoTracking().ToDictionaryAsync(s => s.Id, s => s.Name_en);
+        var lineDtos = lines.Select(l => new ExpenseLineItemDto
+        {
+            Id = l.Id, CategoryGroupId = l.CategoryGroupId, CategoryGroupName = grpNames.GetValueOrDefault(l.CategoryGroupId, ""),
+            SubCategoryId = l.SubCategoryId, SubCategoryName = subNames.GetValueOrDefault(l.SubCategoryId, ""),
+            FunctionalClass = l.FunctionalClass, Amount = l.Amount, Description = l.Description,
+        }).ToList();
+
         return new ExpenseDto
         {
             Id = e.Id, Type = e.Type, Status = e.Status, Amount = e.Amount, Description = e.Description,
             MinistryId = e.MinistryId, MinistryName = minName,
-            CategoryGroupId = e.CategoryGroupId, CategoryGroupName = grpName,
+            LineCount = lineDtos.Count,
-            SubCategoryId = e.SubCategoryId, SubCategoryName = subName,
+            PrimaryCategoryName = lineDtos.Count > 0 ? lineDtos[0].CategoryGroupName : "",
-            VendorName = e.VendorName, MemberId = e.MemberId, MemberName = memName,
+            VendorName = e.VendorName, MemberId = e.MemberId, MemberName = memberName, MemberNickName = memberNickName,
             ExpenseDate = e.ExpenseDate.ToString("yyyy-MM-dd"), HasReceipt = e.ReceiptBlobPath != null,
             CheckNumber = e.CheckNumber, Notes = e.Notes, ReviewNotes = e.ReviewNotes,
-            SubmittedBy = e.SubmittedBy, SubmittedAt = e.SubmittedAt, ReviewedAt = e.ReviewedAt, PaidAt = e.PaidAt,
+            ReviewedByName = reviewerName, ReviewedAt = e.ReviewedAt,
-            FunctionalClass = e.FunctionalClass,
+            SubmittedBy = e.SubmittedBy, SubmittedAt = e.SubmittedAt, PaidAt = e.PaidAt,
+            PayeeId = e.PayeeId,
+            Lines = lineDtos,
         };
     }
 
+    // Lines are the source of truth: ≥1 line, each with a category/subcategory and a positive amount.
+    private static void ValidateLines(List<ExpenseLineInput> lines)
+    {
+        if (lines is null || lines.Count == 0)
+            throw new InvalidOperationException("An expense must have at least one line.");
+        foreach (var l in lines)
+        {
+            if (l.CategoryGroupId <= 0 || l.SubCategoryId <= 0)
+                throw new InvalidOperationException("Each expense line needs a category group and subcategory.");
+            if (l.Amount <= 0)
+                throw new InvalidOperationException("Each expense line amount must be greater than zero.");
+            if (l.FunctionalClass is not null && !FunctionalClasses.All.Contains(l.FunctionalClass))
+                throw new InvalidOperationException($"Invalid functional class '{l.FunctionalClass}'.");
+        }
+    }
+
+    private static List<ExpenseLine> BuildLines(List<ExpenseLineInput> inputs) =>
+        inputs.Select(l => new ExpenseLine
+        {
+            CategoryGroupId = l.CategoryGroupId, SubCategoryId = l.SubCategoryId,
+            FunctionalClass = l.FunctionalClass, Amount = l.Amount, Description = l.Description,
+        }).ToList();
+
     public async Task<int> CreateAsync(CreateExpenseRequest r, bool isFinance)
     {
+        ValidateLines(r.Lines);
         var e = new Expense
         {
-            MinistryId = r.MinistryId, CategoryGroupId = r.CategoryGroupId, SubCategoryId = r.SubCategoryId,
+            MinistryId = r.MinistryId,
-            Type = r.Type, Amount = r.Amount, Description = r.Description, VendorName = r.VendorName,
+            Type = r.Type, Amount = r.Lines.Sum(l => l.Amount), Description = r.Description, VendorName = r.VendorName,
             CheckNumber = r.CheckNumber, ExpenseDate = r.ExpenseDate, Notes = r.Notes,
-            FunctionalClass = r.FunctionalClass,
+            Lines = BuildLines(r.Lines),
         };
 
         if (r.Type == "VendorPayment")
@@ -161,6 +275,7 @@ public class ExpenseService : IExpenseService
             e.VendorName = null;
         }
 
+        e.PayeeId = r.PayeeId;
         _db.Expenses.Add(e);
         await _db.SaveChangesAsync();
         return e.Id;
@@ -174,16 +289,21 @@ public class ExpenseService : IExpenseService
 
     public async Task UpdateAsync(int id, UpdateExpenseRequest r, bool isFinance)
     {
+        ValidateLines(r.Lines);
         // FirstOrDefaultAsync (not FindAsync) so the soft-delete query filter applies.
-        var e = await _db.Expenses.FirstOrDefaultAsync(x => x.Id == id)
+        var e = await _db.Expenses.Include(x => x.Lines).FirstOrDefaultAsync(x => x.Id == id)
             ?? throw new KeyNotFoundException($"Expense {id} not found.");
-        if (!isFinance && !(e.SubmittedBy == CurrentUserId && (e.Status == "Draft" || e.Status == "PendingApproval")))
+        if (!isFinance && !(e.SubmittedBy == CurrentUserId && (e.Status == "Draft" || e.Status == "PendingApproval" || e.Status == "Rejected")))
-            throw new InvalidOperationException("You can only edit your own draft or pending reimbursements.");
+            throw new InvalidOperationException("You can only edit your own draft, pending, or rejected reimbursements.");
 
-        e.MinistryId = r.MinistryId; e.CategoryGroupId = r.CategoryGroupId; e.SubCategoryId = r.SubCategoryId;
+        e.MinistryId = r.MinistryId; e.Description = r.Description; e.CheckNumber = r.CheckNumber;
-        e.Amount = r.Amount; e.Description = r.Description; e.CheckNumber = r.CheckNumber;
+        e.ExpenseDate = r.ExpenseDate; e.Notes = r.Notes; e.PayeeId = r.PayeeId;
-        e.ExpenseDate = r.ExpenseDate; e.Notes = r.Notes; e.FunctionalClass = r.FunctionalClass;
         if (e.Type == "VendorPayment") e.VendorName = r.VendorName;
+
+        // Replace the line set wholesale (lines are owned by the header), recompute the total.
+        _db.ExpenseLines.RemoveRange(e.Lines);
+        e.Lines = BuildLines(r.Lines);
+        e.Amount = r.Lines.Sum(l => l.Amount);
         await _db.SaveChangesAsync();
     }
 
@@ -206,8 +326,11 @@ public class ExpenseService : IExpenseService
     {
         var e = await RequireAsync(id);
         if (e.SubmittedBy != CurrentUserId) throw new InvalidOperationException("Only the submitter can submit this reimbursement.");
-        if (e.Status != "Draft") throw new InvalidOperationException($"Cannot submit from status '{e.Status}'.");
+        // Draft (first submit) or Rejected (re-submit after fixing the flagged issue, e.g. a clearer receipt).
+        if (e.Status != "Draft" && e.Status != "Rejected") throw new InvalidOperationException($"Cannot submit from status '{e.Status}'.");
         e.Status = "PendingApproval"; e.SubmittedAt = DateTimeOffset.UtcNow;
+        // Clear the prior review so the expense returns to a clean pending state.
+        e.ReviewedBy = null; e.ReviewedAt = null; e.ReviewNotes = null;
         await _db.SaveChangesAsync();
     }
 
@@ -230,6 +353,11 @@ public class ExpenseService : IExpenseService
         if (e.Status != "PendingApproval") throw new InvalidOperationException($"Cannot reject from status '{e.Status}'.");
         e.Status = "Rejected"; e.ReviewedBy = CurrentUserId; e.ReviewedAt = DateTimeOffset.UtcNow; e.ReviewNotes = reviewNotes;
         await _db.SaveChangesAsync();
+
+        _audit.Write(
+            AuditActions.ExpenseRejected, AuditCategories.Business, LogLevelEnum.Information,
+            entityName: nameof(Expense), entityId: e.Id.ToString(),
+            summary: $"Expense #{e.Id} rejected: {e.Description} — {reviewNotes}");
     }
 
     public async Task PayAsync(int id, string? checkNumber, DateOnly? paidAt)
@@ -248,8 +376,8 @@ public class ExpenseService : IExpenseService
     public async Task SaveReceiptAsync(int id, Stream content, string fileName, bool isFinance)
     {
         var e = await RequireAsync(id);
-        if (!isFinance && !(e.SubmittedBy == CurrentUserId && (e.Status == "Draft" || e.Status == "PendingApproval")))
+        if (!isFinance && !(e.SubmittedBy == CurrentUserId && (e.Status == "Draft" || e.Status == "PendingApproval" || e.Status == "Rejected")))
-            throw new InvalidOperationException("You can only attach receipts to your own draft or pending reimbursements.");
+            throw new InvalidOperationException("You can only attach receipts to your own draft, pending, or rejected reimbursements.");
 
         var safe = Path.GetFileName(fileName).Replace(' ', '_');
         var path = $"finance/receipts/{e.ExpenseDate.Year}/{e.ExpenseDate.Month}/{e.Id}-{safe}";

API/ROLAC.API/Services/ExpenseSnapshotService.cs

@@ -0,0 +1,165 @@
+using System.Security.Claims;
+using Microsoft.AspNetCore.Http;
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Expense;
+using ROLAC.API.Entities;
+
+namespace ROLAC.API.Services;
+
+public class ExpenseSnapshotService : IExpenseSnapshotService
+{
+    private readonly AppDbContext _db;
+    private readonly IHttpContextAccessor _http;
+    public ExpenseSnapshotService(AppDbContext db, IHttpContextAccessor http)
+    { _db = db; _http = http; }
+
+    // The JWT carries the user id in the "sub" claim (NameClaimType="sub", MapInboundClaims=false),
+    // so ClaimTypes.NameIdentifier is absent at runtime. Check NameIdentifier first (unit tests set it),
+    // then fall back to "sub" (real tokens). Required for the self-ownership guard to work in production.
+    private string CurrentUserId =>
+        _http.HttpContext?.User.FindFirstValue(ClaimTypes.NameIdentifier)
+        ?? _http.HttpContext?.User.FindFirstValue("sub")
+        ?? "system";
+
+    public async Task<List<ExpenseSnapshotDto>> GetAllAsync()
+    {
+        var snaps = await _db.ExpenseSnapshots.AsNoTracking()
+            .OrderByDescending(s => s.CreatedAt).ThenByDescending(s => s.Id)
+            .ToListAsync();
+        if (snaps.Count == 0) return new();
+
+        var ids = snaps.Select(s => s.Id).ToList();
+        var lines = await _db.ExpenseSnapshotLines.AsNoTracking()
+            .Where(l => ids.Contains(l.SnapshotId)).ToListAsync();
+        var linesBySnapshot = lines.GroupBy(l => l.SnapshotId).ToDictionary(g => g.Key, g => g.ToList());
+
+        var minNames = await _db.Ministries.AsNoTracking().ToDictionaryAsync(m => m.Id, m => $"{m.Name_en} / {m.Name_zh}");
+        var creatorNames = await ResolveUserNamesAsync(snaps.Select(s => s.CreatedBy));
+
+        return snaps.Select(s =>
+        {
+            linesBySnapshot.TryGetValue(s.Id, out var ls);
+            return new ExpenseSnapshotDto
+            {
+                Id = s.Id, Name = s.Name, MinistryId = s.MinistryId,
+                MinistryName = minNames.GetValueOrDefault(s.MinistryId, ""),
+                Description = s.Description, VendorName = s.VendorName,
+                CheckNumber = s.CheckNumber, Notes = s.Notes,
+                TotalAmount = ls?.Sum(l => l.Amount) ?? 0,
+                LineCount = ls?.Count ?? 0,
+                CreatedByName = creatorNames.GetValueOrDefault(s.CreatedBy),
+                CreatedAt = s.CreatedAt,
+            };
+        }).ToList();
+    }
+
+    public async Task<ExpenseSnapshotDto?> GetByIdAsync(int id)
+    {
+        var s = await _db.ExpenseSnapshots.AsNoTracking().FirstOrDefaultAsync(x => x.Id == id);
+        if (s is null) return null;
+
+        var lines = await _db.ExpenseSnapshotLines.AsNoTracking()
+            .Where(l => l.SnapshotId == id).OrderBy(l => l.Id).ToListAsync();
+        var minName = await _db.Ministries.Where(m => m.Id == s.MinistryId).Select(m => m.Name_en).FirstOrDefaultAsync() ?? "";
+        var grpNames = await _db.ExpenseCategoryGroups.AsNoTracking().ToDictionaryAsync(g => g.Id, g => g.Name_en);
+        var subNames = await _db.ExpenseSubCategories.AsNoTracking().ToDictionaryAsync(x => x.Id, x => x.Name_en);
+        var creatorName = (await ResolveUserNamesAsync(new[] { s.CreatedBy })).GetValueOrDefault(s.CreatedBy);
+
+        return new ExpenseSnapshotDto
+        {
+            Id = s.Id, Name = s.Name, MinistryId = s.MinistryId, MinistryName = minName,
+            Description = s.Description, VendorName = s.VendorName, CheckNumber = s.CheckNumber, Notes = s.Notes,
+            TotalAmount = lines.Sum(l => l.Amount), LineCount = lines.Count,
+            CreatedByName = creatorName, CreatedAt = s.CreatedAt,
+            Lines = lines.Select(l => new ExpenseSnapshotLineDto
+            {
+                CategoryGroupId = l.CategoryGroupId, CategoryGroupName = grpNames.GetValueOrDefault(l.CategoryGroupId, ""),
+                SubCategoryId = l.SubCategoryId, SubCategoryName = subNames.GetValueOrDefault(l.SubCategoryId, ""),
+                FunctionalClass = l.FunctionalClass, Amount = l.Amount, Description = l.Description,
+            }).ToList(),
+        };
+    }
+
+    public async Task<int> CreateAsync(CreateExpenseSnapshotRequest r)
+    {
+        ValidateLines(r.Lines);
+        var s = new ExpenseSnapshot
+        {
+            Name = r.Name.Trim(), MinistryId = r.MinistryId, Description = r.Description,
+            VendorName = r.VendorName, CheckNumber = r.CheckNumber, Notes = r.Notes,
+            Lines = BuildLines(r.Lines),
+        };
+        _db.ExpenseSnapshots.Add(s);
+        await _db.SaveChangesAsync();
+        return s.Id;
+    }
+
+    public async Task UpdateAsync(int id, UpdateExpenseSnapshotRequest r)
+    {
+        ValidateLines(r.Lines);
+        var s = await _db.ExpenseSnapshots.Include(x => x.Lines).FirstOrDefaultAsync(x => x.Id == id)
+            ?? throw new KeyNotFoundException($"Snapshot {id} not found.");
+
+        s.Name = r.Name.Trim(); s.MinistryId = r.MinistryId; s.Description = r.Description;
+        s.VendorName = r.VendorName; s.CheckNumber = r.CheckNumber; s.Notes = r.Notes;
+
+        _db.ExpenseSnapshotLines.RemoveRange(s.Lines);
+        s.Lines = BuildLines(r.Lines);
+        await _db.SaveChangesAsync();
+    }
+
+    public async Task DeleteAsync(int id)
+    {
+        var s = await _db.ExpenseSnapshots.FirstOrDefaultAsync(x => x.Id == id)
+            ?? throw new KeyNotFoundException($"Snapshot {id} not found.");
+        s.IsDeleted = true; s.DeletedAt = DateTimeOffset.UtcNow; s.DeletedBy = CurrentUserId;
+        await _db.SaveChangesAsync();
+    }
+
+    private static void ValidateLines(List<ExpenseLineInput> lines)
+    {
+        if (lines is null || lines.Count == 0)
+            throw new InvalidOperationException("A snapshot must have at least one line.");
+        foreach (var l in lines)
+        {
+            if (l.CategoryGroupId <= 0 || l.SubCategoryId <= 0)
+                throw new InvalidOperationException("Each snapshot line needs a category group and subcategory.");
+            if (l.Amount <= 0)
+                throw new InvalidOperationException("Each snapshot line amount must be greater than zero.");
+            if (l.FunctionalClass is not null && !FunctionalClasses.All.Contains(l.FunctionalClass))
+                throw new InvalidOperationException($"Invalid functional class '{l.FunctionalClass}'.");
+        }
+    }
+
+    private static List<ExpenseSnapshotLine> BuildLines(List<ExpenseLineInput> inputs) =>
+        inputs.Select(l => new ExpenseSnapshotLine
+        {
+            CategoryGroupId = l.CategoryGroupId, SubCategoryId = l.SubCategoryId,
+            FunctionalClass = l.FunctionalClass, Amount = l.Amount, Description = l.Description,
+        }).ToList();
+
+    // Resolve actor user ids (AppUser.Id, stored in CreatedBy) to a display name: the linked
+    // Member's full name when present, otherwise the account email. Mirrors ExpenseService.
+    private async Task<Dictionary<string, string>> ResolveUserNamesAsync(IEnumerable<string?> userIds)
+    {
+        var ids = userIds.Where(id => !string.IsNullOrEmpty(id)).Select(id => id!).Distinct().ToList();
+        if (ids.Count == 0) return new();
+
+        var users = await _db.Users.AsNoTracking()
+            .Where(u => ids.Contains(u.Id))
+            .Select(u => new { u.Id, u.Email, u.MemberId })
+            .ToListAsync();
+
+        var memberIds = users.Where(u => u.MemberId != null).Select(u => u.MemberId!.Value).ToHashSet();
+        var memberNames = await _db.Members.AsNoTracking()
+            .Where(m => memberIds.Contains(m.Id))
+            .ToDictionaryAsync(m => m.Id, m => $"{m.FirstName_en} {m.LastName_en}".Trim());
+
+        return users.ToDictionary(
+            u => u.Id,
+            u => u.MemberId != null && memberNames.TryGetValue(u.MemberId.Value, out var name) && name.Length > 0
+                ? name
+                : (u.Email ?? u.Id));
+    }
+}

API/ROLAC.API/Services/FinanceDashboardService.cs

@@ -54,16 +54,23 @@ public class FinanceDashboardService : IFinanceDashboardService
     {
         var q = PaidApproved(from, to);
         if (ministryId.HasValue) q = q.Where(e => e.MinistryId == ministryId.Value);
-        if (categoryGroupId.HasValue) q = q.Where(e => e.CategoryGroupId == categoryGroupId.Value);
 
-        // Group by the deepest level whose parent id is supplied.
+        // Lines belonging to the scoped (Paid+Approved, optionally ministry-filtered) expenses.
+        var scopedLines = from l in _db.ExpenseLines
+                          join e in q on l.ExpenseId equals e.Id
+                          select l;
+
+        // Group by the deepest level whose parent id is supplied. Category levels aggregate
+        // over LINES (line amounts); the ministry level uses the header total to avoid
+        // double-counting a multi-line expense across its lines.
         List<(int Id, decimal Amount)> grouped;
         if (categoryGroupId.HasValue)
-            grouped = (await q.GroupBy(e => e.SubCategoryId)
+            grouped = (await scopedLines.Where(l => l.CategoryGroupId == categoryGroupId.Value)
+                .GroupBy(l => l.SubCategoryId)
                 .Select(g => new { Id = g.Key, Amount = g.Sum(x => x.Amount) }).ToListAsync())
                 .Select(x => (x.Id, x.Amount)).ToList();
         else if (ministryId.HasValue)
-            grouped = (await q.GroupBy(e => e.CategoryGroupId)
+            grouped = (await scopedLines.GroupBy(l => l.CategoryGroupId)
                 .Select(g => new { Id = g.Key, Amount = g.Sum(x => x.Amount) }).ToListAsync())
                 .Select(x => (x.Id, x.Amount)).ToList();
         else

API/ROLAC.API/Services/Form1099/Form1099FormService.cs

@@ -0,0 +1,160 @@
+using System.Globalization;
+using System.Text;
+using DevExpress.Office;
+using DevExpress.XtraRichEdit;
+using DevExpress.XtraRichEdit.API.Native;
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Payee;
+using ROLAC.API.Entities;
+
+namespace ROLAC.API.Services;
+
+/// <summary>
+/// Produces recipient-facing 1099 outputs: a plain-paper Copy B 1099-NEC PDF (rendered with the
+/// DevExpress RichEdit/Office API, mirroring <c>CheckPrintService</c>) and a filing-data CSV.
+/// </summary>
+public class Form1099FormService : I1099FormService
+{
+    private readonly IForm1099ReportService _report;
+    private readonly IPayee1099Service _payees;
+    private readonly AppDbContext _db;
+
+    public Form1099FormService(IForm1099ReportService report, IPayee1099Service payees, AppDbContext db)
+    {
+        _report = report;
+        _payees = payees;
+        _db = db;
+    }
+
+    public async Task<(Stream stream, string contentType, string fileName)> RenderCopyBAsync(int payeeId, int taxYear)
+    {
+        var payee = await _payees.GetByIdAsync(payeeId)
+            ?? throw new InvalidOperationException($"Payee {payeeId} not found.");
+
+        var church = await _db.ChurchProfiles.AsNoTracking().OrderBy(x => x.Id).FirstOrDefaultAsync()
+            ?? new ChurchProfile { Name = "Church" };
+
+        // Box 1 (Nonemployee compensation) = sum of this payee's NEC-1 payments for the year.
+        var detail = await _report.GetRecipientDetailAsync(payeeId, taxYear);
+        var box1Nec = detail?.Payments
+            .Where(payment => payment.BoxCode == Entities.Form1099.BoxNec1)
+            .Sum(payment => payment.Amount) ?? 0m;
+
+        using var server = new RichEditDocumentServer();
+        var document = server.Document;
+        document.BeginUpdate();
+        try
+        {
+            document.Unit = DocumentUnit.Inch;
+            var section = document.Sections[0];
+            section.Page.Width = 8.5f;
+            section.Page.Height = 11f;
+            section.Margins.Left = section.Margins.Right = 0.8f;
+            section.Margins.Top = section.Margins.Bottom = 0.8f;
+
+            document.AppendHtmlText(BuildCopyBHtml(church, payee, taxYear, box1Nec));
+        }
+        finally
+        {
+            document.EndUpdate();
+        }
+
+        var stream = new MemoryStream();
+        server.ExportToPdf(stream);
+        stream.Position = 0;
+        return (stream, "application/pdf", $"1099-NEC-{payeeId}-{taxYear}.pdf");
+    }
+
+    public async Task<(Stream stream, string contentType, string fileName)> ExportFilingCsvAsync(int taxYear)
+    {
+        var summary = await _report.GetAnnualSummaryAsync(taxYear);
+        var builder = new StringBuilder();
+        builder.AppendLine("LegalName,TinLast4,W9Status,Box1_NEC,Box1_Rents,Total,MeetsThreshold");
+        foreach (var row in summary.Rows)
+        {
+            builder.AppendLine(string.Join(",",
+                Csv(row.LegalName), Csv(row.TinLast4 ?? ""), Csv(row.W9Status),
+                row.NecTotal.ToString(CultureInfo.InvariantCulture),
+                row.RentsTotal.ToString(CultureInfo.InvariantCulture),
+                row.GrandTotal.ToString(CultureInfo.InvariantCulture),
+                row.MeetsThreshold ? "Y" : "N"));
+        }
+
+        var bytes = Encoding.UTF8.GetBytes(builder.ToString());
+        return (new MemoryStream(bytes), "text/csv", $"1099-filing-{taxYear}.csv");
+
+        static string Csv(string value) => value.Contains(',') || value.Contains('"')
+            ? "\"" + value.Replace("\"", "\"\"") + "\"" : value;
+    }
+
+    private static string BuildCopyBHtml(ChurchProfile church, Payee1099Dto payee, int taxYear, decimal box1Nec)
+    {
+        var payerAddress = JoinAddress(church.Address, church.City, church.State, church.ZipCode);
+        var recipientAddress = JoinAddress(
+            JoinLines(payee.AddressLine1, payee.AddressLine2), payee.City, payee.State, payee.Zip);
+
+        var payerEin  = string.IsNullOrWhiteSpace(church.PayerEin) ? "" : church.PayerEin;
+        var maskedTin = string.IsNullOrWhiteSpace(payee.TinLast4) ? "" : $"***-**-{payee.TinLast4}";
+
+        return
+            "<div style=\"font-family:Arial;font-size:11pt;color:#111;\">" +
+            $"<h2 style=\"text-align:center;margin:0;\">Form 1099-NEC &mdash; Copy B (For Recipient)</h2>" +
+            $"<p style=\"text-align:center;margin:4px 0 16px 0;\"><b>Tax Year {taxYear}</b><br/>Nonemployee Compensation</p>" +
+
+            "<table border=\"1\" cellspacing=\"0\" cellpadding=\"6\" width=\"100%\" style=\"border-collapse:collapse;\">" +
+
+            "<tr><td width=\"50%\" valign=\"top\">" +
+            "<b>PAYER&rsquo;s name, address</b><br/>" +
+            $"{Encode(church.Name)}<br/>{payerAddress}" +
+            "</td>" +
+            "<td width=\"50%\" valign=\"top\">" +
+            $"<b>PAYER&rsquo;s TIN (EIN)</b><br/>{Encode(payerEin)}" +
+            "</td></tr>" +
+
+            "<tr><td valign=\"top\">" +
+            "<b>RECIPIENT&rsquo;s name, address</b><br/>" +
+            $"{Encode(payee.LegalName)}<br/>{recipientAddress}" +
+            "</td>" +
+            "<td valign=\"top\">" +
+            $"<b>RECIPIENT&rsquo;s TIN</b><br/>{Encode(maskedTin)}" +
+            "</td></tr>" +
+
+            "<tr><td colspan=\"2\">" +
+            "<b>Box 1 &mdash; Nonemployee compensation</b><br/>" +
+            $"<span style=\"font-size:14pt;\"><b>{Encode(FormatCurrency(box1Nec))}</b></span>" +
+            "</td></tr>" +
+
+            "</table>" +
+
+            "<p style=\"font-size:8pt;color:#555;margin-top:12px;\">" +
+            "This is important tax information and is being furnished to the recipient. " +
+            "Recipient&rsquo;s taxpayer identification number is shown masked for security." +
+            "</p>" +
+            "</div>";
+    }
+
+    private static string Encode(string? text) => System.Net.WebUtility.HtmlEncode(text ?? "");
+
+    private static string FormatCurrency(decimal amount) =>
+        amount.ToString("C2", CultureInfo.GetCultureInfo("en-US"));
+
+    private static string? JoinLines(string? line1, string? line2)
+    {
+        var parts = new[] { line1, line2 }.Where(part => !string.IsNullOrWhiteSpace(part));
+        var joined = string.Join(", ", parts);
+        return string.IsNullOrWhiteSpace(joined) ? null : joined;
+    }
+
+    // Builds an HTML address block; each text part is HTML-encoded and the line break (<br/>) is literal.
+    private static string JoinAddress(string? address, string? city, string? state, string? zip)
+    {
+        var cityLine = string.Join(", ",
+            new[] { city, string.Join(" ", new[] { state, zip }.Where(part => !string.IsNullOrWhiteSpace(part))) }
+            .Where(part => !string.IsNullOrWhiteSpace(part)));
+        var lines = new[] { address, cityLine }
+            .Where(part => !string.IsNullOrWhiteSpace(part))
+            .Select(Encode);
+        return string.Join("<br/>", lines);
+    }
+}

API/ROLAC.API/Services/Form1099/I1099FormService.cs

@@ -0,0 +1,10 @@
+namespace ROLAC.API.Services;
+
+public interface I1099FormService
+{
+    /// <summary>Recipient Copy B 1099-NEC PDF for one payee/year (plain paper).</summary>
+    Task<(Stream stream, string contentType, string fileName)> RenderCopyBAsync(int payeeId, int taxYear);
+
+    /// <summary>Filing-data CSV (one row per reportable recipient) for IRIS/accountant.</summary>
+    Task<(Stream stream, string contentType, string fileName)> ExportFilingCsvAsync(int taxYear);
+}

API/ROLAC.API/Services/Form1099ReportService.cs

@@ -0,0 +1,134 @@
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Finance;
+using ROLAC.API.Entities;
+
+namespace ROLAC.API.Services;
+
+/// <summary>
+/// Read-only aggregation producing the year-end 1099 recipient summary. CASH BASIS:
+/// only Paid expenses whose PaidAt falls in the tax year, attributed to a tracked payee,
+/// on a line whose category maps to a 1099 box (sub ?? group). Unmapped lines are excluded.
+/// </summary>
+public class Form1099ReportService : IForm1099ReportService
+{
+    private readonly AppDbContext _db;
+    public Form1099ReportService(AppDbContext db) => _db = db;
+
+    public async Task<List<Form1099BoxDto>> GetBoxesAsync() =>
+        await _db.Form1099Boxes.AsNoTracking().Where(b => b.IsActive)
+            .OrderBy(b => b.SortOrder)
+            .Select(b => new Form1099BoxDto
+            {
+                Id = b.Id, BoxCode = b.BoxCode, Name_en = b.Name_en,
+                Name_zh = b.Name_zh, FormType = b.FormType, SortOrder = b.SortOrder,
+            }).ToListAsync();
+
+    /// <summary>
+    /// Pulls the reportable expense lines for the tax year and materializes them (anonymous
+    /// projection -&gt; ToListAsync -&gt; in-memory map), mirroring Form990ReportService so the SQL
+    /// translation stays simple on Npgsql. The tax year is a half-open UTC range
+    /// [Jan 1 taxYear, Jan 1 taxYear+1), deterministic regardless of server timezone and matching
+    /// how Expense.PaidAt is written (midnight UTC). Unmapped lines (no 1099 box) are dropped here
+    /// so callers always receive reportable lines.
+    /// </summary>
+    private async Task<List<PaidLine>> LoadReportableLinesAsync(int taxYear)
+    {
+        var start = new DateTimeOffset(new DateTime(taxYear, 1, 1), TimeSpan.Zero);
+        var end   = start.AddYears(1);
+        var raw = await (
+            from e in _db.Expenses.Where(e => e.Status == "Paid" && e.PaidAt != null
+                                              && e.PaidAt >= start && e.PaidAt < end && e.PayeeId != null)
+            join p   in _db.Payee1099s.Where(p => p.Is1099Tracked) on e.PayeeId equals p.Id
+            join l   in _db.ExpenseLines          on e.Id              equals l.ExpenseId
+            join sub in _db.ExpenseSubCategories  on l.SubCategoryId   equals sub.Id
+            join grp in _db.ExpenseCategoryGroups on l.CategoryGroupId equals grp.Id
+            select new
+            {
+                PayeeId = p.Id,
+                p.LegalName,
+                p.TinLast4,
+                p.W9Status,
+                PaidAt = e.PaidAt!.Value,
+                e.Description,
+                GroupName = grp.Name_en,
+                SubName   = sub.Name_en,
+                l.Amount,
+                BoxId = sub.Form1099BoxId ?? grp.Form1099BoxId,
+            }).ToListAsync();
+
+        return raw.Where(x => x.BoxId != null)
+            .Select(x => new PaidLine
+            {
+                PayeeId      = x.PayeeId,
+                LegalName    = x.LegalName,
+                TinLast4     = x.TinLast4,
+                W9Status     = x.W9Status,
+                PaidAt       = x.PaidAt,
+                Description  = x.Description,
+                CategoryName = x.GroupName + " / " + x.SubName,
+                Amount       = x.Amount,
+                BoxId        = x.BoxId,
+            }).ToList();
+    }
+
+    public async Task<Form1099SummaryDto> GetAnnualSummaryAsync(int taxYear)
+    {
+        var boxes = await _db.Form1099Boxes.AsNoTracking().ToDictionaryAsync(b => b.Id, b => b.BoxCode);
+        var lines = await LoadReportableLinesAsync(taxYear);
+
+        var dto = new Form1099SummaryDto { TaxYear = taxYear };
+        foreach (var g in lines.GroupBy(x => x.PayeeId))
+        {
+            var first = g.First();
+            var nec   = g.Where(x => boxes.GetValueOrDefault(x.BoxId!.Value) == Form1099.BoxNec1).Sum(x => x.Amount);
+            var rents = g.Where(x => boxes.GetValueOrDefault(x.BoxId!.Value) == Form1099.BoxMisc1).Sum(x => x.Amount);
+            var w9Missing = first.W9Status != Form1099.W9Status.OnFile;
+            var meets = nec >= Form1099.ReportingThreshold || rents >= Form1099.ReportingThreshold;
+            dto.Rows.Add(new Form1099RecipientRowDto
+            {
+                PayeeId = first.PayeeId, LegalName = first.LegalName, TinLast4 = first.TinLast4,
+                W9Status = first.W9Status, NecTotal = nec, RentsTotal = rents,
+                GrandTotal = nec + rents, MeetsThreshold = meets, W9Missing = w9Missing,
+            });
+        }
+        dto.Rows = dto.Rows.OrderByDescending(r => r.GrandTotal).ThenBy(r => r.LegalName).ToList();
+        dto.TotalReportable       = dto.Rows.Sum(r => r.GrandTotal);
+        dto.RecipientsAtThreshold = dto.Rows.Count(r => r.MeetsThreshold);
+        dto.RecipientsMissingW9   = dto.Rows.Count(r => r.W9Missing);
+        return dto;
+    }
+
+    public async Task<Form1099RecipientDetailDto?> GetRecipientDetailAsync(int payeeId, int taxYear)
+    {
+        var payee = await _db.Payee1099s.AsNoTracking().FirstOrDefaultAsync(p => p.Id == payeeId);
+        if (payee is null) return null;
+        var boxes = await _db.Form1099Boxes.AsNoTracking().ToDictionaryAsync(b => b.Id, b => b.BoxCode);
+        var lines = (await LoadReportableLinesAsync(taxYear)).Where(x => x.PayeeId == payeeId).ToList();
+
+        return new Form1099RecipientDetailDto
+        {
+            PayeeId = payee.Id, LegalName = payee.LegalName, TinLast4 = payee.TinLast4,
+            W9Status = payee.W9Status, TaxYear = taxYear,
+            Payments = lines.OrderBy(x => x.PaidAt).Select(x => new Form1099PaymentDto
+            {
+                PaidDate = DateOnly.FromDateTime(x.PaidAt.Date).ToString("yyyy-MM-dd"),
+                Description = x.Description, CategoryName = x.CategoryName,
+                BoxCode = boxes.GetValueOrDefault(x.BoxId!.Value) ?? "", Amount = x.Amount,
+            }).ToList(),
+        };
+    }
+
+    private sealed class PaidLine
+    {
+        public int            PayeeId      { get; set; }
+        public string         LegalName    { get; set; } = "";
+        public string?        TinLast4     { get; set; }
+        public string         W9Status     { get; set; } = "";
+        public DateTimeOffset PaidAt       { get; set; }
+        public string         Description  { get; set; } = "";
+        public string         CategoryName { get; set; } = "";
+        public decimal        Amount       { get; set; }
+        public int?           BoxId        { get; set; }
+    }
+}

API/ROLAC.API/Services/Form990ReportService.cs

@@ -8,7 +8,7 @@ namespace ROLAC.API.Services;
 /// <summary>
 /// Read-only aggregation that produces the IRS Form 990 Part IX Statement of Functional
 /// Expenses. Expense scope matches FinanceDashboardService: Paid + Approved only.
-/// Single function per expense (direct-charge); no cost splitting.
+/// Each expense line is categorized independently, so one invoice can span multiple lines.
 /// </summary>
 public class Form990ReportService : IForm990ReportService
 {
@@ -40,13 +40,14 @@ public class Form990ReportService : IForm990ReportService
 
         var rows = await (
             from e in expenses
+            join l   in _db.ExpenseLines           on e.Id              equals l.ExpenseId
             join m   in _db.Ministries            on e.MinistryId      equals m.Id
-            join sub in _db.ExpenseSubCategories   on e.SubCategoryId   equals sub.Id
+            join sub in _db.ExpenseSubCategories   on l.SubCategoryId   equals sub.Id
-            join grp in _db.ExpenseCategoryGroups  on e.CategoryGroupId equals grp.Id
+            join grp in _db.ExpenseCategoryGroups  on l.CategoryGroupId equals grp.Id
             select new
             {
-                e.Amount,
+                l.Amount,
-                e.FunctionalClass,
+                l.FunctionalClass,
                 MinistryDefault = m.DefaultFunctionalClass,
                 SubLineId   = sub.Form990LineId,
                 GroupLineId = grp.Form990LineId,

API/ROLAC.API/Services/IExpenseSnapshotService.cs

@@ -0,0 +1,11 @@
+using ROLAC.API.DTOs.Expense;
+namespace ROLAC.API.Services;
+
+public interface IExpenseSnapshotService
+{
+    Task<List<ExpenseSnapshotDto>> GetAllAsync();
+    Task<ExpenseSnapshotDto?>      GetByIdAsync(int id);
+    Task<int>                      CreateAsync(CreateExpenseSnapshotRequest r);
+    Task                           UpdateAsync(int id, UpdateExpenseSnapshotRequest r);
+    Task                           DeleteAsync(int id);
+}

API/ROLAC.API/Services/IForm1099ReportService.cs

@@ -0,0 +1,9 @@
+using ROLAC.API.DTOs.Finance;
+namespace ROLAC.API.Services;
+
+public interface IForm1099ReportService
+{
+    Task<List<Form1099BoxDto>> GetBoxesAsync();
+    Task<Form1099SummaryDto> GetAnnualSummaryAsync(int taxYear);
+    Task<Form1099RecipientDetailDto?> GetRecipientDetailAsync(int payeeId, int taxYear);
+}

API/ROLAC.API/Services/IPayee1099Service.cs

@@ -0,0 +1,17 @@
+using ROLAC.API.DTOs.Payee;
+namespace ROLAC.API.Services;
+
+public interface IPayee1099Service
+{
+    Task<List<Payee1099ListItemDto>> GetAllAsync(bool includeInactive);
+    Task<Payee1099Dto?> GetByIdAsync(int id);
+    Task<int> CreateAsync(SavePayee1099Request r);
+    Task UpdateAsync(int id, SavePayee1099Request r);
+    Task DeleteAsync(int id);
+    /// <summary>Full decrypted TIN. Caller must be authorized (gated at controller).</summary>
+    Task<string?> RevealTinAsync(int id);
+    /// <summary>Stores the uploaded W-9 blob and records its path. Throws KeyNotFoundException if the payee is missing.</summary>
+    Task SaveW9Async(int id, Stream content, string fileName);
+    /// <summary>Opens the stored W-9 blob; null when none is attached.</summary>
+    Task<(Stream stream, string contentType)?> OpenW9Async(int id);
+}

API/ROLAC.API/Services/Payee1099Service.cs

@@ -0,0 +1,162 @@
+using Microsoft.EntityFrameworkCore;
+using ROLAC.API.Data;
+using ROLAC.API.DTOs.Payee;
+using ROLAC.API.Entities;
+using ROLAC.API.Services.Security;
+using ROLAC.API.Services.Storage;
+
+namespace ROLAC.API.Services;
+
+public class Payee1099Service : IPayee1099Service
+{
+    private readonly AppDbContext _db;
+    private readonly ITinProtector _tin;
+    private readonly IFileStorage _storage;
+
+    public Payee1099Service(AppDbContext db, ITinProtector tin, IFileStorage storage)
+    {
+        _db      = db;
+        _tin     = tin;
+        _storage = storage;
+    }
+
+    public async Task<List<Payee1099ListItemDto>> GetAllAsync(bool includeInactive)
+    {
+        var q = _db.Payee1099s.AsNoTracking().Include(p => p.Member).AsQueryable();
+        if (!includeInactive) q = q.Where(p => p.IsActive);
+        return await q.OrderBy(p => p.LegalName).Select(p => new Payee1099ListItemDto
+        {
+            Id               = p.Id,
+            LegalName        = p.LegalName,
+            DisplayName      = p.DisplayName,
+            MemberId         = p.MemberId,
+            MemberName       = p.Member != null ? p.Member.FirstName_en + " " + p.Member.LastName_en : null,
+            TaxClassification = p.TaxClassification,
+            Is1099Tracked    = p.Is1099Tracked,
+            TinType          = p.TinType,
+            TinLast4         = p.TinLast4,
+            W9Status         = p.W9Status,
+            IsActive         = p.IsActive,
+        }).ToListAsync();
+    }
+
+    public async Task<Payee1099Dto?> GetByIdAsync(int id)
+    {
+        var p = await _db.Payee1099s.AsNoTracking().Include(x => x.Member).FirstOrDefaultAsync(x => x.Id == id);
+        if (p is null) return null;
+        return new Payee1099Dto
+        {
+            Id               = p.Id,
+            LegalName        = p.LegalName,
+            DisplayName      = p.DisplayName,
+            MemberId         = p.MemberId,
+            MemberName       = p.Member != null ? $"{p.Member.FirstName_en} {p.Member.LastName_en}" : null,
+            TaxClassification = p.TaxClassification,
+            Is1099Tracked    = p.Is1099Tracked,
+            TinType          = p.TinType,
+            TinLast4         = p.TinLast4,
+            W9Status         = p.W9Status,
+            IsActive         = p.IsActive,
+            AddressLine1     = p.AddressLine1,
+            AddressLine2     = p.AddressLine2,
+            City             = p.City,
+            State            = p.State,
+            Zip              = p.Zip,
+            Email            = p.Email,
+            Phone            = p.Phone,
+            W9ReceivedDate   = p.W9ReceivedDate?.ToString("yyyy-MM-dd"),
+            HasW9Document    = p.W9BlobPath != null,
+            Notes            = p.Notes,
+        };
+    }
+
+    public async Task<int> CreateAsync(SavePayee1099Request r)
+    {
+        var p = new Payee1099();
+        Apply(p, r);
+        _db.Payee1099s.Add(p);
+        await _db.SaveChangesAsync();
+        return p.Id;
+    }
+
+    public async Task UpdateAsync(int id, SavePayee1099Request r)
+    {
+        var p = await _db.Payee1099s.FirstOrDefaultAsync(x => x.Id == id)
+            ?? throw new KeyNotFoundException($"Payee1099 {id} not found.");
+        Apply(p, r);
+        await _db.SaveChangesAsync();
+    }
+
+    public async Task DeleteAsync(int id)
+    {
+        var p = await _db.Payee1099s.FirstOrDefaultAsync(x => x.Id == id)
+            ?? throw new KeyNotFoundException($"Payee1099 {id} not found.");
+        p.IsDeleted  = true;
+        p.DeletedAt  = DateTimeOffset.UtcNow;
+        await _db.SaveChangesAsync();
+    }
+
+    public async Task<string?> RevealTinAsync(int id)
+    {
+        var p = await _db.Payee1099s.AsNoTracking().FirstOrDefaultAsync(x => x.Id == id);
+        return p?.TinEncrypted is null ? null : _tin.Unprotect(p.TinEncrypted);
+    }
+
+    public async Task SaveW9Async(int id, Stream content, string fileName)
+    {
+        var p = await _db.Payee1099s.FirstOrDefaultAsync(x => x.Id == id)
+            ?? throw new KeyNotFoundException($"Payee1099 {id} not found.");
+
+        // Mirror the expense-receipt blob convention: a stable per-record path under a feature folder,
+        // preserving the original extension. Re-uploads overwrite the prior blob.
+        var ext  = Path.GetExtension(fileName);
+        var path = $"finance/w9/{p.Id}{ext}";
+        if (p.W9BlobPath != null && p.W9BlobPath != path)
+            await _storage.DeleteAsync(p.W9BlobPath);
+        var saved = await _storage.SaveAsync(content, path);
+        p.W9BlobPath = saved;
+        await _db.SaveChangesAsync();
+    }
+
+    public async Task<(Stream stream, string contentType)?> OpenW9Async(int id)
+    {
+        var p = await _db.Payee1099s.AsNoTracking().FirstOrDefaultAsync(x => x.Id == id);
+        if (p?.W9BlobPath is null) return null;
+        var stream = await _storage.OpenReadAsync(p.W9BlobPath);
+        if (stream is null) return null;
+        var ext = Path.GetExtension(p.W9BlobPath).ToLowerInvariant();
+        var contentType = ext switch
+        {
+            ".png" => "image/png", ".webp" => "image/webp", ".pdf" => "application/pdf",
+            _ => "image/jpeg",
+        };
+        return (stream, contentType);
+    }
+
+    // Maps request fields onto the entity. A null/blank Tin leaves the existing ciphertext untouched (update case).
+    private void Apply(Payee1099 p, SavePayee1099Request r)
+    {
+        p.LegalName        = r.LegalName;
+        p.DisplayName      = r.DisplayName;
+        p.MemberId         = r.MemberId;
+        p.TaxClassification = r.TaxClassification;
+        p.Is1099Tracked    = r.Is1099Tracked;
+        p.TinType          = r.TinType;
+        p.AddressLine1     = r.AddressLine1;
+        p.AddressLine2     = r.AddressLine2;
+        p.City             = r.City;
+        p.State            = r.State;
+        p.Zip              = r.Zip;
+        p.Email            = r.Email;
+        p.Phone            = r.Phone;
+        p.W9Status         = r.W9Status;
+        p.W9ReceivedDate   = r.W9ReceivedDate;
+        p.IsActive         = r.IsActive;
+        p.Notes            = r.Notes;
+        if (!string.IsNullOrWhiteSpace(r.Tin))
+        {
+            p.TinEncrypted = _tin.Protect(r.Tin);
+            p.TinLast4     = TinProtector.Last4(r.Tin);
+        }
+    }
+}

API/ROLAC.API/Services/Security/ITinProtector.cs

@@ -0,0 +1,8 @@
+namespace ROLAC.API.Services.Security;
+
+/// <summary>Reversible protection for taxpayer identification numbers (SSN/EIN).</summary>
+public interface ITinProtector
+{
+    string Protect(string plaintext);
+    string Unprotect(string ciphertext);
+}

API/ROLAC.API/Services/Security/TinProtector.cs

@@ -0,0 +1,22 @@
+using Microsoft.AspNetCore.DataProtection;
+
+namespace ROLAC.API.Services.Security;
+
+public class TinProtector : ITinProtector
+{
+    private readonly IDataProtector _protector;
+
+    public TinProtector(IDataProtectionProvider provider)
+        => _protector = provider.CreateProtector("Payee1099.Tin");
+
+    public string Protect(string plaintext)    => _protector.Protect(plaintext);
+    public string Unprotect(string ciphertext) => _protector.Unprotect(ciphertext);
+
+    /// <summary>Last four digits of a TIN (ignoring dashes/spaces); null/empty in => null.</summary>
+    public static string? Last4(string? raw)
+    {
+        if (string.IsNullOrWhiteSpace(raw)) return null;
+        var digits = new string(raw.Where(char.IsDigit).ToArray());
+        return digits.Length <= 4 ? digits : digits[^4..];
+    }
+}

API/ROLAC.API/appsettings.json

@@ -41,5 +41,52 @@
   "Line": {
     "ChannelAccessToken": "",
     "ChannelSecret": ""
+  },
+  "Gemini": {
+    "ApiKey": "",
+    "Model": "gemini-2.5-flash-lite",
+    "BaseUrl": "https://generativelanguage.googleapis.com/v1beta"
+  },
+  "Claude": {
+    "ApiKey": "",
+    "Model": "claude-haiku-4-5-20251001",
+    "BaseUrl": "https://api.anthropic.com/v1",
+    "AnthropicVersion": "2023-06-01"
+  },
+  "Ai": {
+    "Provider": "Claude"
+  },
+  "CheckPrint": {
+    "//": "Field coordinates (inches) for pre-printed three-stub check stock. X = from page left edge; OffsetY = within the field's stub, added to the stub origin. Tune to match your stock, then restart — no recompile.",
+    "Layout": {
+      "//cal": "TextInset* compensates for the fixed inset the TextBox adds around its text so configured X/Y == actual ink. To recalibrate, set both to 0, print, measure the drift past a known X/Y, and enter the differences here.",
+      "TextInsetX": 0.13,
+      "TextInsetY": 0.15,
+      "CheckOriginY": 0.0,
+      "Receipt1OriginY": 3.67,
+      "Receipt2OriginY": 7.33,
+      "Payee":         { "X": 1.1, "OffsetY": 1.35, "FontSize": 11, "Bold": true },
+      "AmountNumeric": { "X": 7.0, "OffsetY": 1.35, "FontSize": 12, "Bold": true },
+      "AmountWords":   { "X": 0.30, "OffsetY": 1.67, "FontSize": 10 },
+      "Memo":          { "X": 0.60, "OffsetY": 2.85, "FontSize": 9 },
+      "CheckDate":     { "X": 7.00, "OffsetY": 0.90, "FontSize": 10 },
+      "ReceiptPayee":  { "X": 1.00, "OffsetY": 0.30, "FontSize": 10, "Bold": true },
+      "ReceiptAmount": { "X": 6.50, "OffsetY": 0.30, "FontSize": 10, "Bold": true },
+      "ReceiptMemo":   { "X": 1.00, "OffsetY": 0.60, "FontSize": 9 },
+      "ReceiptDate":   { "X": 6.50, "OffsetY": 0.60, "FontSize": 9 },
+      "Grid": {
+        "OriginX": 0.60,
+        "OffsetY": 1.10,
+        "RowHeight": 0.22,
+        "ColumnGap": 0.30,
+        "DateWidth": 0.85,
+        "DescWidth": 2.10,
+        "AmountWidth": 0.80,
+        "ShowGridHeaders": true,
+        "HeaderOffsetY": 0.88,
+        "OverflowOffsetY": 2.55,
+        "FontSize": 8.5
+      }
+    }
   }
 }

APP/src/app/app.routes.ts

@@ -14,6 +14,7 @@ import { GivingsPageComponent } from './features/giving/pages/givings-page/givin
 import { OfferingSessionPageComponent } from './features/giving/pages/offering-session-page/offering-session-page.component';
 import { ExpenseCategoriesPageComponent } from './features/expense/pages/expense-categories-page/expense-categories-page.component';
 import { ExpensesPageComponent } from './features/expense/pages/expenses-page/expenses-page.component';
+import { ExpenseSnapshotsPageComponent } from './features/expense/pages/expense-snapshots-page/expense-snapshots-page.component';
 import { MyReimbursementsPageComponent } from './features/expense/pages/my-reimbursements-page/my-reimbursements-page.component';
 import { MonthlyStatementPageComponent } from './features/expense/pages/monthly-statement-page/monthly-statement-page.component';
 import { FinanceDashboardPageComponent } from './features/finance-dashboard/pages/finance-dashboard-page/finance-dashboard-page.component';
@@ -21,6 +22,8 @@ import { DisbursementPageComponent } from './features/disbursement/pages/disburs
 import { CheckRegisterPageComponent } from './features/disbursement/pages/check-register-page/check-register-page.component';
 import { ChurchProfilePageComponent } from './features/disbursement/pages/church-profile-page/church-profile-page.component';
 import { Form990ReportPageComponent } from './features/finance-report/pages/form990-report-page/form990-report-page.component';
+import { Form1099ReportPageComponent } from './features/finance-report/pages/form1099-report-page/form1099-report-page.component';
+import { Payee1099PageComponent } from './features/payee1099/pages/payee-1099-page/payee-1099-page.component';
 import { AttendanceCounterPageComponent } from './features/meal-attendance/pages/attendance-counter-page/attendance-counter-page.component';
 import { OfferingEntryMobilePageComponent } from './features/giving/pages/offering-entry-mobile-page/offering-entry-mobile-page.component';
 import { SystemLogsPageComponent } from './features/logging/pages/system-logs-page/system-logs-page.component';
@@ -162,6 +165,17 @@ export const routes: Routes = [
                     title: 'Expenses', titleZh: '支出', section: 'Finance',
                 },
             },
+            {
+                path: 'finance/expense-snapshots',
+                component: ExpenseSnapshotsPageComponent,
+                canActivate: [PermissionGuard],
+                data: {
+                    // Snapshots are a write-only management surface (the API gates every action on
+                    // Expenses:Write), so require write — a read-only user has nothing to do here.
+                    permission: { module: PermissionModules.Expenses, action: 'write' },
+                    title: 'Expense Snapshots', titleZh: '費用範本', section: 'Finance',
+                },
+            },
             {
                 path: 'finance/expense-categories',
                 component: ExpenseCategoriesPageComponent,
@@ -216,6 +230,24 @@ export const routes: Routes = [
                     title: 'Form 990 — Functional Expenses', titleZh: 'Form 990 功能性費用表', section: 'Finance',
                 },
             },
+            {
+                path: 'finance/payee-1099',
+                component: Payee1099PageComponent,
+                canActivate: [PermissionGuard],
+                data: {
+                    permission: { module: PermissionModules.Form1099, action: 'read' },
+                    title: '1099 Recipients', titleZh: '1099 收款人', section: 'Finance',
+                },
+            },
+            {
+                path: 'finance/form1099-report',
+                component: Form1099ReportPageComponent,
+                canActivate: [PermissionGuard],
+                data: {
+                    permission: { module: PermissionModules.Form1099, action: 'read' },
+                    title: '1099 Year-End Report', titleZh: '1099 年度報表', section: 'Finance',
+                },
+            },
         ]
     },
 

APP/src/app/core/models/permission.model.ts

@@ -33,6 +33,7 @@ export const PermissionModules = {
     SystemLogs:        'SystemLogs',
     AuditLogs:         'AuditLogs',
     Settings:          'Settings',
+    Form1099:          'Form1099',
 } as const;
 
 /** A required permission, used in route data and the *appHasPermission directive. */

APP/src/app/features/disbursement/models/disbursement.model.ts

@@ -48,7 +48,12 @@ export interface ChurchProfileDto {
   id: number; name: string; nameZh: string | null; phone: string | null;
   email: string | null; website: string | null; address: string | null; city: string | null;
   state: string | null; zipCode: string | null; bankName: string | null;
-  bankAccountNumber: string | null; bankRoutingNumber: string | null; nextCheckNumber: number;
+  bankAccountNumber: string | null; bankRoutingNumber: string | null; payerEin: string | null; nextCheckNumber: number;
+  aiProvider: string;
+  claudeModel: string | null; claudeApiKeyMasked: string | null;
+  geminiModel: string | null; geminiApiKeyMasked: string | null;
 }
 
-export type UpdateChurchProfileRequest = Omit<ChurchProfileDto, 'id'>;
+export type UpdateChurchProfileRequest =
+  Omit<ChurchProfileDto, 'id' | 'claudeApiKeyMasked' | 'geminiApiKeyMasked'>
+  & { claudeApiKey: string | null; geminiApiKey: string | null };

APP/src/app/features/disbursement/pages/church-profile-page/church-profile-page.component.html

@@ -55,6 +55,10 @@
               Routing # / 路由號碼
               <kendo-textbox [(ngModel)]="model.bankRoutingNumber"></kendo-textbox>
             </label>
+            <label class="flex flex-col gap-1">
+              Payer EIN / 雇主識別號 (EIN)
+              <kendo-textbox [(ngModel)]="model.payerEin" placeholder="XX-XXXXXXX"></kendo-textbox>
+            </label>
             <label class="flex flex-col gap-1">
               Next Check # / 下一張支票號碼
               <kendo-numerictextbox [(ngModel)]="model.nextCheckNumber" [min]="1" [decimals]="0" format="#"></kendo-numerictextbox>
@@ -82,5 +86,52 @@
         <app-notification-settings-tab></app-notification-settings-tab>
       </ng-template>
     </kendo-tabstrip-tab>
+
+    <!-- ── Tab 4: AI Settings (Settings permission) ───────────────────────── -->
+    <kendo-tabstrip-tab title="AI Settings / AI 設定" *appHasPermission="settingsPermission">
+      <ng-template kendoTabContent>
+        <div *ngIf="model" class="max-w-3xl pt-4">
+          <div class="grid grid-cols-1 md:grid-cols-2 gap-x-4 gap-y-3">
+            <label class="flex flex-col gap-1 md:col-span-2">
+              AI Provider / AI 供應商
+              <kendo-dropdownlist
+                [data]="aiProviders" textField="text" valueField="value" [valuePrimitive]="true"
+                [(ngModel)]="model.aiProvider"></kendo-dropdownlist>
+            </label>
+
+            <label class="flex flex-col gap-1">
+              Claude Model / Claude 模型
+              <kendo-textbox [(ngModel)]="model.claudeModel"></kendo-textbox>
+            </label>
+            <label class="flex flex-col gap-1">
+              Claude API Key / Claude 金鑰
+              <input kendoTextBox type="password" autocomplete="new-password"
+                     [(ngModel)]="claudeApiKeyInput"
+                     [placeholder]="model.claudeApiKeyMasked || 'Enter key / 輸入金鑰'" />
+            </label>
+
+            <label class="flex flex-col gap-1">
+              Gemini Model / Gemini 模型
+              <kendo-textbox [(ngModel)]="model.geminiModel"></kendo-textbox>
+            </label>
+            <label class="flex flex-col gap-1">
+              Gemini API Key / Gemini 金鑰
+              <input kendoTextBox type="password" autocomplete="new-password"
+                     [(ngModel)]="geminiApiKeyInput"
+                     [placeholder]="model.geminiApiKeyMasked || 'Enter key / 輸入金鑰'" />
+            </label>
+
+            <p class="md:col-span-2 text-sm" style="color:#6b7280;">
+              Leave a key blank to keep the saved one. / 金鑰留空表示沿用已儲存的設定。
+            </p>
+          </div>
+
+          <div class="flex items-center gap-3 mt-4">
+            <button kendoButton themeColor="primary" [disabled]="saving" (click)="save()">Save / 儲存</button>
+            <span class="text-sm" style="color:#065f46;">{{ savedMsg }}</span>
+          </div>
+        </div>
+      </ng-template>
+    </kendo-tabstrip-tab>
   </kendo-tabstrip>
 </div>

APP/src/app/features/disbursement/pages/church-profile-page/church-profile-page.component.ts

@@ -4,8 +4,9 @@ import { FormsModule } from '@angular/forms';
 import { ButtonsModule } from '@progress/kendo-angular-buttons';
 import { InputsModule } from '@progress/kendo-angular-inputs';
 import { LayoutModule } from '@progress/kendo-angular-layout';
+import { DropDownsModule } from '@progress/kendo-angular-dropdowns';
 import { DisbursementApiService } from '../../services/disbursement-api.service';
-import { ChurchProfileDto } from '../../models/disbursement.model';
+import { ChurchProfileDto, UpdateChurchProfileRequest } from '../../models/disbursement.model';
 import { HasPermissionDirective } from '../../../../core/directives/has-permission.directive';
 import { PermissionModules } from '../../../../core/models/permission.model';
 import { SiteSettingsTabComponent } from '../../../settings/components/site-settings-tab/site-settings-tab.component';
@@ -15,7 +16,7 @@ import { NotificationSettingsTabComponent } from '../../../settings/components/n
   selector: 'app-church-profile-page',
   standalone: true,
   imports: [
-    CommonModule, FormsModule, ButtonsModule, InputsModule, LayoutModule,
+    CommonModule, FormsModule, ButtonsModule, InputsModule, LayoutModule, DropDownsModule,
     HasPermissionDirective, SiteSettingsTabComponent, NotificationSettingsTabComponent,
   ],
   templateUrl: './church-profile-page.component.html',
@@ -25,6 +26,15 @@ export class ChurchProfilePageComponent implements OnInit {
   saving = false;
   savedMsg = '';
 
+  /** Bound to the password inputs; blank means "keep the saved key". Reset after each save. */
+  claudeApiKeyInput = '';
+  geminiApiKeyInput = '';
+
+  readonly aiProviders = [
+    { text: 'Claude', value: 'Claude' },
+    { text: 'Gemini', value: 'Gemini' },
+  ];
+
   /** Settings module gates the Site / Notification tabs. */
   readonly settingsPermission = { module: PermissionModules.Settings, action: 'read' as const };
 
@@ -38,9 +48,21 @@ export class ChurchProfilePageComponent implements OnInit {
     if (!this.model || this.saving) return;
     this.saving = true;
     this.savedMsg = '';
-    const { id, ...req } = this.model;
+    const { id, claudeApiKeyMasked, geminiApiKeyMasked, ...rest } = this.model;
+    const req: UpdateChurchProfileRequest = {
+      ...rest,
+      claudeApiKey: this.claudeApiKeyInput.trim() || null,
+      geminiApiKey: this.geminiApiKeyInput.trim() || null,
+    };
     this.api.updateChurchProfile(req).subscribe({
-      next: () => { this.saving = false; this.savedMsg = 'Saved / 已儲存'; },
+      next: () => {
+        this.saving = false;
+        this.savedMsg = 'Saved / 已儲存';
+        // Clear the key inputs and reload so the masked placeholders reflect the new keys.
+        this.claudeApiKeyInput = '';
+        this.geminiApiKeyInput = '';
+        this.api.getChurchProfile().subscribe(p => (this.model = p));
+      },
       error: () => {
         // Error message is shown globally by httpErrorInterceptor.
         this.saving = false;

APP/src/app/features/expense/components/expense-form-dialog/expense-form-dialog.component.html

@@ -1,5 +1,22 @@
-<kendo-dialog [title]="title" (close)="cancel.emit()" [width]="560" [maxWidth]="'95vw'" [maxHeight]="'90vh'">
+<kendo-dialog [title]="title" (close)="cancel.emit()" [width]="showReceiptPanel ? 1200 : 760" [maxWidth]="'95vw'"
-  <div class="grid grid-cols-1 md:grid-cols-2 gap-x-4 gap-y-3">
+  [maxHeight]="'90vh'">
+  <!-- Two columns on desktop: form on the left, receipt preview on the right. Stacks on mobile. -->
+  <div class="flex flex-col gap-4 md:flex-row">
+
+    <div class="flex-1 min-w-0 grid grid-cols-1 md:grid-cols-2 gap-x-4 gap-y-3">
+
+      <!-- Snapshot tools (vendor mode): quick-load a saved template, or save the current form -->
+      <div *ngIf="showSnapshotTools" class="md:col-span-2 flex flex-wrap items-end gap-2 rounded border border-gray-200 bg-gray-50 p-2">
+        <label class="flex flex-1 min-w-[14rem] flex-col gap-1">範本 / Load from snapshot
+          <kendo-dropdownlist [data]="snapshots" textField="name" valueField="id" [valuePrimitive]="true"
+            [(ngModel)]="selectedSnapshotId" (valueChange)="applySnapshot($event)"
+            [defaultItem]="{ id: null, name: '-- 選擇範本 / Select a saved snapshot --' }">
+          </kendo-dropdownlist>
+        </label>
+        <button kendoButton fillMode="outline" themeColor="primary" type="button"
+          [disabled]="!isValid" (click)="openSnapshotPrompt()"
+          title="Save the current form as a reusable snapshot / 儲存為範本">💾 存為範本 / Save as snapshot</button>
+      </div>
 
       <!-- Continuous entry: keep member/ministry/category/date after each save (on-behalf reimbursement only) -->
       <label *ngIf="showContinueEntry" class="flex items-center gap-2 md:col-span-2">
@@ -7,91 +24,141 @@
         <span>連續登打 / Continuous Entry</span>
       </label>
 
+      <!-- Description (with AI assist: translate to English + suggest a category) -->
+      <div class="flex flex-col gap-1 md:col-span-2">
+        <div class="flex items-end justify-between gap-2">
+          <label class="flex flex-1 flex-col gap-1">Description
+            <kendo-textbox [(ngModel)]="form.description"
+              placeholder="Brief description of expense / 費用說明（可輸入中文）"></kendo-textbox>
+          </label>
+          <button kendoButton fillMode="outline" themeColor="primary" type="button"
+            [disabled]="!form.description.trim() || aiLoading" (click)="requestAiAssist()"
+            title="Translate to English and suggest a category / 翻譯並建議分類">
+            {{ aiLoading ? '思考中… / Thinking…' : '✨ AI 建議' }}
+          </button>
+        </div>
+
+        <!-- Suggestion card: the "suggest & confirm" step — user applies or dismisses -->
+        <div *ngIf="hasAiSuggestion" class="rounded border border-blue-200 bg-blue-50 p-3 flex flex-col gap-2 text-sm">
+          <div class="font-semibold text-blue-800">AI 建議 / Suggestion</div>
+          <div *ngIf="aiSuggestedDescription" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">說明 / Description:</span>
+            <span class="font-medium">{{ aiSuggestedDescription }}</span>
+          </div>
+          <div *ngIf="aiSuggestion?.groupLabel" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">分類 / Category:</span>
+            <span class="font-medium">{{ aiSuggestion?.groupLabel }}<span *ngIf="aiSuggestion?.subLabel"> → {{
+                aiSuggestion?.subLabel }}</span></span>
+          </div>
+          <div class="text-xs text-gray-500">信心 / Confidence: {{ (aiSuggestion?.confidence ?? 0) * 100 | number:'1.0-0'
+            }}%</div>
+          <div class="flex gap-2">
+            <button kendoButton themeColor="primary" size="small" type="button" (click)="applyAiSuggestion()">套用 /
+              Apply</button>
+            <button kendoButton fillMode="flat" size="small" type="button" (click)="dismissAiSuggestion()">忽略 /
+              Dismiss</button>
+          </div>
+        </div>
+      </div>
       <!-- Member picker (finance creating on behalf of a member) -->
       <label *ngIf="allowMemberPick" class="flex flex-col gap-1 md:col-span-2">Member
-      <kendo-dropdownlist
+        <kendo-dropdownlist [data]="memberResults" textField="displayName" valueField="id" [valuePrimitive]="true"
-          [data]="memberResults"
+          [filterable]="true" (filterChange)="onMemberFilter($event)" [(ngModel)]="form.memberId"
-          textField="displayName"
-          valueField="id"
-          [valuePrimitive]="true"
-          [filterable]="true"
-          (filterChange)="onMemberFilter($event)"
-          [(ngModel)]="form.memberId"
           placeholder="Search member by name">
         </kendo-dropdownlist>
       </label>
 
       <!-- Ministry -->
       <label class="flex flex-col gap-1">Ministry
-      <kendo-dropdownlist
+        <kendo-dropdownlist [data]="ministries" textField="label" valueField="id" [valuePrimitive]="true"
-          [data]="ministries"
+          [(ngModel)]="form.ministryId" [defaultItem]="{ id: null, label: '-- Select ministry --/請選擇事工' }">
-          textField="label"
-          valueField="id"
-          [valuePrimitive]="true"
-          [(ngModel)]="form.ministryId"
-          [defaultItem]="{ id: null, label: '-- Select ministry --/請選擇事工' }">
         </kendo-dropdownlist>
       </label>
 
-    <!-- Category Group -->
-    <label class="flex flex-col gap-1">Category Group
-      <kendo-dropdownlist
-          [data]="groups"
-          textField="label"
-          valueField="id"
-          [valuePrimitive]="true"
-          [(ngModel)]="form.categoryGroupId"
-          (valueChange)="onGroupChange($event)"
-          [defaultItem]="{ id: null, label: '-- Select group --/請選擇大類' }">
-      </kendo-dropdownlist>
-    </label>
-
-    <!-- Sub-Category -->
-    <label class="flex flex-col gap-1">Sub-Category
-      <kendo-dropdownlist
-          [data]="subs"
-          textField="label"
-          valueField="id"
-          [valuePrimitive]="true"
-          [(ngModel)]="form.subCategoryId"
-          [defaultItem]="{ id: null, label: '-- Select sub-category --/請選擇子項' }"
-          [disabled]="!form.categoryGroupId">
-      </kendo-dropdownlist>
-    </label>
-
-    <!-- Functional Class override -->
-    <label class="flex flex-col gap-1">
-      <span>Functional Class / 功能別</span>
-      <kendo-dropdownlist
-          [data]="functionalClassOptions"
-          textField="label"
-          valueField="value"
-          [valuePrimitive]="true"
-          [defaultItem]="{ value: null, label: '(Inherit ministry / 沿用事工)' }"
-          [(ngModel)]="form.functionalClass">
-      </kendo-dropdownlist>
-    </label>
-
-    <!-- Amount -->
-    <label class="flex flex-col gap-1">Amount
-      <kendo-numerictextbox
-          [(ngModel)]="form.amount"
-          [min]="0"
-          [format]="'c2'">
-      </kendo-numerictextbox>
-    </label>
-
       <!-- Expense Date -->
       <label class="flex flex-col gap-1">Expense Date
         <kendo-datepicker [(ngModel)]="form.expenseDate"></kendo-datepicker>
       </label>
 
-    <!-- Description -->
+      <!-- Category lines: one invoice can span several categories -->
-    <label class="flex flex-col gap-1 md:col-span-2">Description
+      <div class="md:col-span-2 flex flex-col gap-2">
-      <kendo-textbox [(ngModel)]="form.description" placeholder="Brief description of expense"></kendo-textbox>
+        <div class="flex items-center justify-between">
+          <span class="font-semibold">明細 / Line Items</span>
+          <span class="text-sm text-gray-600">合計 / Total: {{ totalAmount | currency }}</span>
+        </div>
+
+        <div *ngFor="let line of lines; let i = index" class="flex flex-col gap-3 rounded border border-gray-200 p-3">
+          <!-- Line header: number + remove -->
+          <div class="flex items-center justify-between">
+            <span class="text-sm font-medium text-gray-600">明細 {{ i + 1 }} / Item {{ i + 1 }}</span>
+            <button kendoButton fillMode="outline" themeColor="primary" size="small" type="button"
+              [disabled]="!line.description.trim() || line.aiLoading" (click)="requestLineAiAssist(line)"
+              title="Translate this line and suggest a category / 翻譯並建議此列分類">
+              {{ line.aiLoading ? '思考中… / Thinking…' : '✨ AI 建議此列' }}
+            </button>
+            <button kendoButton fillMode="flat" themeColor="error" size="small" [disabled]="lines.length === 1"
+              (click)="removeLine(i)" title="Remove line / 刪除此列">✕ 刪除</button>
+          </div>
+
+          <!-- Row 1: Category Group + Sub-Category -->
+          <div class="grid grid-cols-1 md:grid-cols-2 gap-3">
+            <label class="flex flex-col gap-1">Category Group
+              <kendo-dropdownlist [data]="groups" textField="label" valueField="id" [valuePrimitive]="true"
+                [(ngModel)]="line.categoryGroupId" (valueChange)="onLineGroupChange(line, $event)"
+                [defaultItem]="{ id: null, label: '-- Select group --/請選擇大類' }">
+              </kendo-dropdownlist>
             </label>
 
-    <!-- Vendor mode: vendor name + check number -->
+            <label class="flex flex-col gap-1">Sub-Category
+              <kendo-dropdownlist [data]="line.subs" textField="label" valueField="id" [valuePrimitive]="true"
+                [(ngModel)]="line.subCategoryId" [defaultItem]="{ id: null, label: '-- Select sub-category --/請選擇子項' }"
+                [disabled]="!line.categoryGroupId">
+              </kendo-dropdownlist>
+            </label>
+          </div>
+
+          <!-- Row 2: Description (optional) + Amount -->
+          <div class="grid grid-cols-1 md:grid-cols-2 gap-3">
+            <label class="flex flex-col gap-1"><span>Description / 說明 <span class="text-gray-400">(Optional)</span></span>
+              <kendo-textbox [(ngModel)]="line.description" placeholder="e.g. 點心、文具…"></kendo-textbox>
+            </label>
+
+            <label class="flex flex-col gap-1">Amount
+              <kendo-numerictextbox [(ngModel)]="line.amount" [min]="0" [format]="'c2'"></kendo-numerictextbox>
+            </label>
+          </div>
+
+          <!-- Per-line suggestion card: the "suggest & confirm" step for this line -->
+          <div *ngIf="hasLineSuggestion(line)"
+            class="rounded border border-blue-200 bg-blue-50 p-3 flex flex-col gap-2 text-sm">
+            <div class="font-semibold text-blue-800">AI 建議 / Suggestion</div>
+            <div *ngIf="lineSuggestedDescription(line)" class="flex gap-2">
+              <span class="text-gray-500 shrink-0">說明 / Description:</span>
+              <span class="font-medium">{{ lineSuggestedDescription(line) }}</span>
+            </div>
+            <div *ngIf="line.aiSuggestion?.groupLabel" class="flex gap-2">
+              <span class="text-gray-500 shrink-0">分類 / Category:</span>
+              <span class="font-medium">{{ line.aiSuggestion?.groupLabel }}<span *ngIf="line.aiSuggestion?.subLabel"> →
+                  {{ line.aiSuggestion?.subLabel }}</span></span>
+            </div>
+            <div class="text-xs text-gray-500">信心 / Confidence: {{ (line.aiSuggestion?.confidence ?? 0) * 100 |
+              number:'1.0-0' }}%</div>
+            <div class="flex gap-2">
+              <button kendoButton themeColor="primary" size="small" type="button"
+                (click)="applyLineAiSuggestion(line)">套用 / Apply</button>
+              <button kendoButton fillMode="flat" size="small" type="button" (click)="dismissLineAiSuggestion(line)">忽略
+                / Dismiss</button>
+            </div>
+          </div>
+        </div>
+
+        <div>
+          <button kendoButton fillMode="outline" (click)="addLine()">+ 新增一列 / Add Line</button>
+        </div>
+      </div>
+
+
+      <!-- Vendor mode: vendor name + check number + optional 1099 recipient -->
       <ng-container *ngIf="mode === 'vendor'">
         <label class="flex flex-col gap-1">Vendor Name
           <kendo-textbox [(ngModel)]="form.vendorName" placeholder="Payee / vendor name"></kendo-textbox>
@@ -99,6 +166,12 @@
         <label class="flex flex-col gap-1">Check #
           <kendo-textbox [(ngModel)]="form.checkNumber" placeholder="Check number (optional)"></kendo-textbox>
         </label>
+        <label class="flex flex-col gap-1 md:col-span-2">1099 Recipient / 1099 收款人 <span class="text-gray-400 font-normal">(optional)</span>
+          <kendo-dropdownlist [data]="payees" textField="legalName" valueField="id" [valuePrimitive]="true"
+            [defaultItem]="{ id: null, legalName: '— none —' }"
+            [(ngModel)]="form.payeeId">
+          </kendo-dropdownlist>
+        </label>
       </ng-container>
 
       <!-- Reimbursement mode: receipt file input -->
@@ -109,20 +182,62 @@
           from bubbling up to the host, where it would collide with this component's
           @Output() cancel and wrongly close the dialog. See Angular issues #50556 / #13997.
         -->
-        <input
+          <input #receiptInput type="file" accept="image/*,application/pdf" (change)="onFileSelected($event)"
-            #receiptInput
-            type="file"
-            accept="image/*,application/pdf"
-            (change)="onFileSelected($event)"
             (cancel)="$event.stopPropagation()"
             class="block w-full text-sm text-gray-700 file:mr-3 file:py-1 file:px-3 file:rounded file:border-0 file:text-sm file:bg-gray-100 hover:file:bg-gray-200" />
         </label>
       </ng-container>
 
     </div>
+    <!-- /left form column -->
+
+    <!-- Right: receipt preview (shown once a file is selected or an existing receipt is loaded) -->
+    <div *ngIf="showReceiptPanel" class="md:w-[34rem] md:shrink-0 md:border-l md:pl-4 flex flex-col gap-2">
+      <div class="flex items-center justify-between">
+        <span class="font-semibold">收據預覽 / Receipt</span>
+        <!-- Zoom controls (image only; PDF uses the browser viewer's own zoom) -->
+        <div *ngIf="receiptImageUrl" class="flex items-center gap-1">
+          <button kendoButton size="small" fillMode="flat" (click)="zoomOut()" [disabled]="receiptZoom <= minZoom"
+            title="縮小 / Zoom out">−</button>
+          <span class="w-12 text-center text-sm tabular-nums">{{ receiptZoom * 100 | number:'1.0-0' }}%</span>
+          <button kendoButton size="small" fillMode="flat" (click)="zoomIn()" [disabled]="receiptZoom >= maxZoom"
+            title="放大 / Zoom in">＋</button>
+          <button kendoButton size="small" fillMode="flat" (click)="resetZoom()" title="重設 / Reset">⟲</button>
+        </div>
+      </div>
+
+      <!-- Scrollable so a zoomed-in image can be panned for comparison -->
+      <div *ngIf="receiptImageUrl" class="overflow-auto rounded border border-gray-200 bg-gray-50"
+        style="max-height: 72vh;">
+        <img [src]="receiptImageUrl" alt="Receipt preview" [style.width.%]="receiptZoom * 100"
+          class="block max-w-none" />
+      </div>
+
+      <iframe *ngIf="receiptPdfUrl" [src]="receiptPdfUrl" title="Receipt PDF"
+        class="w-full rounded border border-gray-200" style="height: 72vh;"></iframe>
+    </div>
+
+  </div>
+  <!-- /two-column body -->
 
   <kendo-dialog-actions>
     <button kendoButton (click)="cancel.emit()">Cancel</button>
     <button kendoButton themeColor="primary" [disabled]="!isValid" (click)="emitSave()">Save</button>
   </kendo-dialog-actions>
 </kendo-dialog>
+
+<!-- Save-as-snapshot name prompt -->
+<kendo-dialog *ngIf="showSnapshotNamePrompt" title="存為範本 / Save as Snapshot" [width]="420" [maxWidth]="'95vw'"
+  (close)="cancelSnapshotPrompt()">
+  <div class="flex flex-col gap-2 p-2">
+    <label class="flex flex-col gap-1">名稱 / Name
+      <kendo-textbox [(ngModel)]="snapshotName" placeholder="e.g. Monthly Rent — Landlord X"></kendo-textbox>
+    </label>
+    <p class="text-xs text-gray-500">費用日期不會存入範本 / The Expense Date is not saved in a snapshot.</p>
+  </div>
+  <kendo-dialog-actions>
+    <button kendoButton (click)="cancelSnapshotPrompt()">Cancel</button>
+    <button kendoButton themeColor="primary" [disabled]="!snapshotName.trim() || snapshotSaving"
+      (click)="saveSnapshot()">{{ snapshotSaving ? '儲存中… / Saving…' : 'Save' }}</button>
+  </kendo-dialog-actions>
+</kendo-dialog>

APP/src/app/features/expense/components/expense-form-dialog/expense-form-dialog.component.ts

@@ -1,6 +1,7 @@
-import { Component, ElementRef, EventEmitter, Input, OnInit, Output, ViewChild } from '@angular/core';
+import { Component, ElementRef, EventEmitter, Input, OnDestroy, OnInit, Output, ViewChild } from '@angular/core';
 import { CommonModule } from '@angular/common';
 import { FormsModule } from '@angular/forms';
+import { DomSanitizer, SafeResourceUrl } from '@angular/platform-browser';
 import { InputsModule } from '@progress/kendo-angular-inputs';
 import { ButtonsModule } from '@progress/kendo-angular-buttons';
 import { DialogsModule } from '@progress/kendo-angular-dialog';
@@ -8,11 +9,17 @@ import { DropDownsModule } from '@progress/kendo-angular-dropdowns';
 import { DateInputsModule } from '@progress/kendo-angular-dateinputs';
 import { MinistryApiService } from '../../services/ministry-api.service';
 import { ExpenseCategoryApiService } from '../../services/expense-category-api.service';
+import { ExpenseApiService } from '../../services/expense-api.service';
+import { ExpenseSnapshotApiService } from '../../services/expense-snapshot-api.service';
+import { ExpenseSnapshotDto, CreateExpenseSnapshotRequest } from '../../models/expense-snapshot.model';
+import { ExpenseAiService } from '../../services/expense-ai.service';
 import { MemberApiService } from '../../../members/services/member-api.service';
 import { MemberListItemDto, memberDisplayName } from '../../../members/models/member.model';
+import { Payee1099ApiService } from '../../../payee1099/services/payee1099-api.service';
+import { Payee1099ListItem } from '../../../payee1099/models/payee1099.model';
 import {
   MinistryDto, ExpenseCategoryGroupDto, ExpenseSubCategoryDto, ExpenseType, CreateExpenseRequest,
-  ExpenseListItemDto, FunctionalClass,
+  ExpenseDto, FunctionalClass, ExpenseAiSuggestion,
 } from '../../models/expense.model';
 
 export interface ExpenseFormResult {
@@ -25,18 +32,33 @@ export interface ExpenseFormResult {
 /** Flattened member item with a single displayName field for the dropdown. */
 interface MemberOption { id: number; displayName: string; }
 
+/** One editable category line. `subs` holds the sub-category list for this row's chosen group. */
+interface ExpenseLineForm {
+  categoryGroupId: number | null;
+  subCategoryId: number | null;
+  amount: number;
+  description: string;
+  /** Functional class is no longer exposed in the form (too complex for volunteers); it stays
+   *  null = inherit the ministry default. Kept here so existing overrides survive an edit. */
+  functionalClass: FunctionalClass | null;
+  subs: ExpenseSubCategoryDto[];
+  /** Per-line AI assist state (suggest & confirm), independent of the header assist. */
+  aiLoading?: boolean;
+  aiSuggestion?: ExpenseAiSuggestion | null;
+}
+
 @Component({
   selector: 'app-expense-form-dialog',
   standalone: true,
   imports: [CommonModule, FormsModule, InputsModule, ButtonsModule, DialogsModule, DropDownsModule, DateInputsModule],
   templateUrl: './expense-form-dialog.component.html',
 })
-export class ExpenseFormDialogComponent implements OnInit {
+export class ExpenseFormDialogComponent implements OnInit, OnDestroy {
   @Input() mode: 'vendor' | 'reimbursement' = 'reimbursement';
   @Input() allowMemberPick = false;
   @Input() title = 'New Expense';
-  /** When set, the dialog prefills from this row for editing instead of starting blank. */
+  /** When set, the dialog prefills from this expense (with its lines) for editing. */
-  @Input() expense: ExpenseListItemDto | null = null;
+  @Input() expense: ExpenseDto | null = null;
   @Output() save = new EventEmitter<ExpenseFormResult>();
   @Output() cancel = new EventEmitter<void>();
 
@@ -45,19 +67,27 @@ export class ExpenseFormDialogComponent implements OnInit {
 
   ministries: MinistryDto[] = [];
   groups: ExpenseCategoryGroupDto[] = [];
-  subs: ExpenseSubCategoryDto[] = [];
+
+  payees: Payee1099ListItem[] = [];
+
+  /** Saved snapshots (vendor mode only) for the "Load from snapshot" picker. */
+  snapshots: ExpenseSnapshotDto[] = [];
+  /** Picker binding; reset to null after each apply so the same snapshot can be re-picked. */
+  selectedSnapshotId: number | null = null;
+
+  /** "Save as snapshot" name-prompt state. */
+  showSnapshotNamePrompt = false;
+  snapshotName = '';
+  snapshotSaving = false;
+
+  /** Snapshot tools (load/save) are a vendor-payment feature only. */
+  get showSnapshotTools(): boolean { return this.mode === 'vendor'; }
 
   memberResults: MemberOption[] = [];
 
   /** Continuous-entry toggle: keep member/ministry/category/date and the dialog open after each save. */
   continueEntry = false;
 
-  readonly functionalClassOptions: { value: FunctionalClass; label: string }[] = [
-    { value: 'Program',           label: 'Program / 事工服務' },
-    { value: 'ManagementGeneral', label: 'Management & General / 管理' },
-    { value: 'Fundraising',       label: 'Fundraising / 募款' },
-  ];
-
   /** The on-behalf reimbursement create flow is the only place continuous entry applies. */
   get showContinueEntry(): boolean {
     return this.mode === 'reimbursement' && this.allowMemberPick && !this.expense;
@@ -65,56 +95,213 @@ export class ExpenseFormDialogComponent implements OnInit {
 
   form = {
     ministryId: null as number | null,
-    categoryGroupId: null as number | null,
-    subCategoryId: null as number | null,
-    amount: 0,
     description: '',
     vendorName: '',
     checkNumber: '',
     memberId: null as number | null,
+    payeeId: null as number | null,
     expenseDate: new Date(),
-    functionalClass: null as FunctionalClass | null,
   };
+  /** At least one line always; "+ Add line" appends, each line is independently removable down to one. */
+  lines: ExpenseLineForm[] = [this.emptyLine()];
   receipt: File | null = null;
 
+  // ── Receipt preview (right panel) ────────────────────────────────────────
+  /** Blob URL for an image receipt, bound directly to <img [src]>. */
+  receiptImageUrl: string | null = null;
+  /** Sanitized blob URL for a PDF receipt, bound to <iframe [src]>. */
+  receiptPdfUrl: SafeResourceUrl | null = null;
+  /** Raw object URL kept so it can be revoked. */
+  private receiptObjectUrl: string | null = null;
+
+  /** Image zoom factor (1 = fit panel width); lets volunteers blow up a receipt to compare. */
+  receiptZoom = 1;
+  readonly minZoom = 0.5;
+  readonly maxZoom = 5;
+
+  get showReceiptPanel(): boolean { return !!(this.receiptImageUrl || this.receiptPdfUrl); }
+
+  zoomIn(): void { this.receiptZoom = Math.min(this.maxZoom, +(this.receiptZoom + 0.25).toFixed(2)); }
+  zoomOut(): void { this.receiptZoom = Math.max(this.minZoom, +(this.receiptZoom - 0.25).toFixed(2)); }
+  resetZoom(): void { this.receiptZoom = 1; }
+
+  // ── AI assist (translate description + suggest category) ────────────────────
+  /** True while an assist request is in flight (disables the button, shows a spinner label). */
+  aiLoading = false;
+  /** The latest suggestion awaiting the user's Apply/Dismiss decision; null when none is shown. */
+  aiSuggestion: ExpenseAiSuggestion | null = null;
+
   constructor(
     private ministryApi: MinistryApiService,
     private catApi: ExpenseCategoryApiService,
     private memberApi: MemberApiService,
+    private expenseApi: ExpenseApiService,
+    private snapshotApi: ExpenseSnapshotApiService,
+    private aiApi: ExpenseAiService,
+    private payeeApi: Payee1099ApiService,
+    private sanitizer: DomSanitizer,
   ) {}
 
   ngOnInit(): void {
     this.ministryApi.getAll().subscribe(m => (this.ministries = m));
+    this.payeeApi.getAll(false).subscribe(list => (this.payees = list));
+    if (this.showSnapshotTools) this.loadSnapshots();
     this.catApi.getAll(false).subscribe(groups => {
       this.groups = groups;
-      // Populate the sub-category list for the prefilled group so its value displays on edit.
+      // Populate each line's sub-category list once the catalog is loaded (edit mode).
-      if (this.expense) {
+      if (this.expense) this.hydrateLineSubs();
-        this.subs = this.groups.find(group => group.id === this.expense!.categoryGroupId)?.subCategories ?? [];
-      }
     });
-    if (this.expense) this.prefill(this.expense);
+    if (this.expense) {
+      this.prefill(this.expense);
+      // Edit mode: load the existing receipt into the preview panel.
+      if (this.expense.hasReceipt) {
+        this.expenseApi.downloadReceipt(this.expense.id)
+          .subscribe(blob => this.setPreview(blob, blob.type));
+      }
+    }
   }
 
-  private prefill(expense: ExpenseListItemDto): void {
+  ngOnDestroy(): void { this.clearPreview(); }
+
+  private emptyLine(): ExpenseLineForm {
+    return { categoryGroupId: null, subCategoryId: null, amount: 0, description: '', functionalClass: null, subs: [] };
+  }
+
+  private prefill(expense: ExpenseDto): void {
     // expenseDate is a "yyyy-MM-dd" string; build a local Date to avoid a timezone day-shift.
     const [year, month, day] = expense.expenseDate.split('-').map(Number);
     this.form = {
       ministryId: expense.ministryId,
-      categoryGroupId: expense.categoryGroupId,
-      subCategoryId: expense.subCategoryId,
-      amount: expense.amount,
       description: expense.description,
       vendorName: expense.vendorName ?? '',
       checkNumber: expense.checkNumber ?? '',
       memberId: expense.memberId,
+      payeeId: expense.payeeId ?? null,
       expenseDate: new Date(year, month - 1, day),
-      functionalClass: expense.functionalClass ?? null,
     };
+    this.lines = (expense.lines ?? []).map(l => ({
+      categoryGroupId: l.categoryGroupId,
+      subCategoryId: l.subCategoryId,
+      amount: l.amount,
+      description: l.description ?? '',
+      functionalClass: l.functionalClass,
+      subs: [],
+    }));
+    if (this.lines.length === 0) this.lines = [this.emptyLine()];
   }
 
-  onGroupChange(groupId: number | null): void {
+  /** Fill each line's sub-category list from its chosen group (used after the catalog loads on edit). */
-    this.form.subCategoryId = null;
+  private hydrateLineSubs(): void {
-    this.subs = this.groups.find(g => g.id === groupId)?.subCategories ?? [];
+    for (const line of this.lines) {
+      line.subs = this.groups.find(g => g.id === line.categoryGroupId)?.subCategories ?? [];
+    }
+  }
+
+  onLineGroupChange(line: ExpenseLineForm, groupId: number | null): void {
+    line.subCategoryId = null;
+    line.subs = this.groups.find(g => g.id === groupId)?.subCategories ?? [];
+  }
+
+  /** Ask the backend AI to translate the description and suggest a category; show it for confirmation. */
+  requestAiAssist(): void {
+    const text = this.form.description.trim();
+    if (!text || this.aiLoading) return;
+    this.aiLoading = true;
+    this.aiSuggestion = null;
+    this.aiApi.assist(text, this.totalAmount).subscribe({
+      next: suggestion => { this.aiSuggestion = suggestion; this.aiLoading = false; },
+      error: () => { this.aiLoading = false; },
+    });
+  }
+
+  /** True once a suggestion offers at least a translation or a category to apply. */
+  get hasAiSuggestion(): boolean {
+    const s = this.aiSuggestion;
+    return !!s && (!!this.aiSuggestedDescription || s.groupId != null);
+  }
+
+  /** Combine a suggestion's two halves into the "English / 中文" string that Apply writes. */
+  private combineDescription(suggestion: ExpenseAiSuggestion | null | undefined): string {
+    if (!suggestion) return '';
+    const en = suggestion.englishDescription?.trim() ?? '';
+    const zh = suggestion.chineseDescription?.trim() ?? '';
+    if (en && zh) return `${en} / ${zh}`;
+    return en || zh;
+  }
+
+  /** The description that the header Apply will write. */
+  get aiSuggestedDescription(): string {
+    return this.combineDescription(this.aiSuggestion);
+  }
+
+  /**
+   * Apply the suggestion: set the description to "English / 中文" and set the first line's
+   * category/sub. Most expenses are single-line; multi-line users adjust the rest by hand.
+   */
+  applyAiSuggestion(): void {
+    const suggestion = this.aiSuggestion;
+    if (!suggestion) return;
+    if (this.aiSuggestedDescription) this.form.description = this.aiSuggestedDescription;
+    if (suggestion.groupId != null) {
+      const firstLine = this.lines[0];
+      firstLine.categoryGroupId = suggestion.groupId;
+      // Populate the sub-category list for the chosen group, then select the suggested sub.
+      this.onLineGroupChange(firstLine, suggestion.groupId);
+      if (suggestion.subCategoryId != null) firstLine.subCategoryId = suggestion.subCategoryId;
+    }
+    this.aiSuggestion = null;
+  }
+
+  dismissAiSuggestion(): void { this.aiSuggestion = null; }
+
+  // ── Per-line AI assist ──────────────────────────────────────────────────────
+  /** Ask the AI to translate this line's own note and suggest its category, using the line's amount. */
+  requestLineAiAssist(line: ExpenseLineForm): void {
+    const text = line.description.trim();
+    if (!text || line.aiLoading) return;
+    line.aiLoading = true;
+    line.aiSuggestion = null;
+    this.aiApi.assist(text, line.amount).subscribe({
+      next: suggestion => { line.aiSuggestion = suggestion; line.aiLoading = false; },
+      error: () => { line.aiLoading = false; },
+    });
+  }
+
+  /** The description that this line's Apply will write: "English / 中文". */
+  lineSuggestedDescription(line: ExpenseLineForm): string {
+    return this.combineDescription(line.aiSuggestion);
+  }
+
+  /** True once a line suggestion offers a translation or a category to apply. */
+  hasLineSuggestion(line: ExpenseLineForm): boolean {
+    return !!line.aiSuggestion && (!!this.lineSuggestedDescription(line) || line.aiSuggestion.groupId != null);
+  }
+
+  /** Apply this line's suggestion to itself: set its description (bilingual) and category/sub. */
+  applyLineAiSuggestion(line: ExpenseLineForm): void {
+    const suggestion = line.aiSuggestion;
+    if (!suggestion) return;
+    const description = this.lineSuggestedDescription(line);
+    if (description) line.description = description;
+    if (suggestion.groupId != null) {
+      line.categoryGroupId = suggestion.groupId;
+      // Populate the sub-category list for the chosen group, then select the suggested sub.
+      this.onLineGroupChange(line, suggestion.groupId);
+      if (suggestion.subCategoryId != null) line.subCategoryId = suggestion.subCategoryId;
+    }
+    line.aiSuggestion = null;
+  }
+
+  dismissLineAiSuggestion(line: ExpenseLineForm): void { line.aiSuggestion = null; }
+
+  addLine(): void { this.lines.push(this.emptyLine()); }
+
+  removeLine(index: number): void {
+    if (this.lines.length > 1) this.lines.splice(index, 1);
+  }
+
+  get totalAmount(): number {
+    return this.lines.reduce((sum, l) => sum + (l.amount || 0), 0);
   }
 
   onMemberFilter(term: string): void {
@@ -130,12 +317,99 @@ export class ExpenseFormDialogComponent implements OnInit {
 
   onFileSelected(event: Event): void {
     const input = event.target as HTMLInputElement;
-    this.receipt = input.files?.[0] ?? null;
+    const file = input.files?.[0] ?? null;
+    this.receipt = file;
+    if (file) this.setPreview(file, file.type);
+  }
+
+  /** Show a newly-selected file or a fetched existing receipt in the right-hand preview panel. */
+  private setPreview(blob: Blob, contentType: string): void {
+    this.clearPreview();
+    this.receiptZoom = 1;
+    this.receiptObjectUrl = URL.createObjectURL(blob);
+    if (contentType.startsWith('image/')) {
+      this.receiptImageUrl = this.receiptObjectUrl;
+    } else {
+      this.receiptPdfUrl = this.sanitizer.bypassSecurityTrustResourceUrl(this.receiptObjectUrl);
+    }
+  }
+
+  private clearPreview(): void {
+    if (this.receiptObjectUrl) { URL.revokeObjectURL(this.receiptObjectUrl); this.receiptObjectUrl = null; }
+    this.receiptImageUrl = null;
+    this.receiptPdfUrl = null;
+  }
+
+  private loadSnapshots(): void {
+    this.snapshotApi.getAll().subscribe(list => (this.snapshots = list));
+  }
+
+  /** Apply a saved snapshot: prefill header + lines, but keep today's Expense Date. */
+  applySnapshot(snapshotId: number | null): void {
+    if (snapshotId == null) return;
+    this.snapshotApi.getById(snapshotId).subscribe(s => {
+      this.form.ministryId = s.ministryId;
+      this.form.description = s.description;
+      this.form.vendorName = s.vendorName ?? '';
+      this.form.checkNumber = s.checkNumber ?? '';
+      // Expense Date is intentionally NOT taken from the snapshot — leave it as-is (today).
+      this.lines = s.lines.map(line => ({
+        categoryGroupId: line.categoryGroupId,
+        subCategoryId: line.subCategoryId,
+        amount: line.amount,
+        description: line.description ?? '',
+        functionalClass: line.functionalClass,
+        subs: this.groups.find(g => g.id === line.categoryGroupId)?.subCategories ?? [],
+      }));
+      if (this.lines.length === 0) this.lines = [this.emptyLine()];
+      this.selectedSnapshotId = null;
+    });
+  }
+
+  /** Open the name prompt for saving the current form as a snapshot (requires a valid form). */
+  openSnapshotPrompt(): void {
+    if (!this.isValid) return;
+    this.snapshotName = '';
+    this.showSnapshotNamePrompt = true;
+  }
+
+  cancelSnapshotPrompt(): void { this.showSnapshotNamePrompt = false; }
+
+  /** Save the current header + lines as a named snapshot (Expense Date is not stored). */
+  saveSnapshot(): void {
+    const name = this.snapshotName.trim();
+    if (!name || this.snapshotSaving) return;
+    const request: CreateExpenseSnapshotRequest = {
+      name,
+      ministryId: this.form.ministryId!,
+      lines: this.lines.map(l => ({
+        categoryGroupId: l.categoryGroupId!,
+        subCategoryId: l.subCategoryId!,
+        amount: l.amount,
+        functionalClass: l.functionalClass,
+        description: l.description.trim() || null,
+      })),
+      description: this.form.description.trim(),
+      vendorName: this.form.vendorName || null,
+      checkNumber: this.form.checkNumber || null,
+      notes: null,
+    };
+    this.snapshotSaving = true;
+    this.snapshotApi.create(request).subscribe({
+      next: () => {
+        this.snapshotSaving = false;
+        this.showSnapshotNamePrompt = false;
+        this.loadSnapshots();
+      },
+      error: () => { this.snapshotSaving = false; },
+    });
   }
 
   get isValid(): boolean {
-    return !!this.form.ministryId && !!this.form.categoryGroupId && !!this.form.subCategoryId
+    return !!this.form.ministryId
-      && this.form.amount > 0 && this.form.description.trim().length > 0;
+      && this.form.description.trim().length > 0
+      && this.lines.length > 0
+      && this.lines.every(l => !!l.categoryGroupId && !!l.subCategoryId && l.amount > 0);
   }
 
   emitSave(): void {
@@ -145,16 +419,20 @@ export class ExpenseFormDialogComponent implements OnInit {
     const request: CreateExpenseRequest = {
       type: (this.mode === 'vendor' ? 'VendorPayment' : 'StaffReimbursement') as ExpenseType,
       ministryId: this.form.ministryId!,
-      categoryGroupId: this.form.categoryGroupId!,
+      lines: this.lines.map(l => ({
-      subCategoryId: this.form.subCategoryId!,
+        categoryGroupId: l.categoryGroupId!,
-      amount: this.form.amount,
+        subCategoryId: l.subCategoryId!,
+        amount: l.amount,
+        functionalClass: l.functionalClass,
+        description: l.description.trim() || null,
+      })),
       description: this.form.description.trim(),
       vendorName: this.mode === 'vendor' ? (this.form.vendorName || null) : null,
       memberId: this.allowMemberPick ? this.form.memberId : null,
       checkNumber: this.mode === 'vendor' ? (this.form.checkNumber || null) : null,
       expenseDate,
       notes: null,
-      functionalClass: this.form.functionalClass,
+      payeeId: this.form.payeeId,
     };
     // The request and receipt are snapshotted here, so resetting the form right
     // after emitting is safe even though the parent saves asynchronously.
@@ -163,14 +441,14 @@ export class ExpenseFormDialogComponent implements OnInit {
   }
 
   /**
-   * Clear only the per-entry fields, keeping Member, Ministry, Category Group,
+   * Clear only the per-entry fields, keeping Member, Ministry and Expense Date so the
-   * Sub-Category and Expense Date (plus the loaded sub-category list) so the
+   * user can immediately log the next reimbursement. Lines reset to a single blank row.
-   * user can immediately log the next reimbursement.
    */
   private resetForNext(): void {
-    this.form.amount = 0;
+    this.lines = [this.emptyLine()];
     this.form.description = '';
     this.receipt = null;
+    this.clearPreview();
     if (this.receiptInput) this.receiptInput.nativeElement.value = '';
   }
 }

APP/src/app/features/expense/components/expense-review-dialog/expense-review-dialog.component.html

@@ -0,0 +1,108 @@
+<kendo-dialog title="Review Expense / 審核支出" (close)="cancel.emit()"
+  [width]="showReceiptPanel ? 1100 : 620" [maxWidth]="'95vw'" [maxHeight]="'90vh'">
+
+  <div *ngIf="loading" class="p-6 text-center text-gray-500">Loading… / 載入中…</div>
+
+  <div *ngIf="!loading && expense" class="flex flex-col gap-4 md:flex-row">
+
+    <!-- Left: read-only expense detail -->
+    <div class="flex-1 min-w-0 flex flex-col gap-3">
+      <div class="grid grid-cols-2 gap-x-4 gap-y-2 text-sm">
+        <div class="text-gray-500">Date / 日期</div><div>{{ expense.expenseDate }}</div>
+        <div class="text-gray-500">Ministry / 事工</div><div>{{ expense.ministryName }}</div>
+        <div class="text-gray-500">Payee / 收款人</div>
+        <div>
+          <ng-container *ngIf="expense.vendorName; else memberPayee">{{ expense.vendorName }}</ng-container>
+          <ng-template #memberPayee>
+            <ng-container *ngIf="expense.memberName; else dash">
+              <div *ngIf="expense.memberNickName">{{ expense.memberNickName }}</div>
+              <div [class.text-gray-500]="expense.memberNickName" [class.text-xs]="expense.memberNickName">{{ expense.memberName }}</div>
+            </ng-container>
+            <ng-template #dash>—</ng-template>
+          </ng-template>
+        </div>
+        <div class="text-gray-500">Description / 說明</div><div>{{ expense.description }}</div>
+        <div class="text-gray-500">Status / 狀態</div><div>{{ expense.status }}</div>
+      </div>
+
+      <!-- Line items -->
+      <div class="flex flex-col gap-1">
+        <div class="font-semibold text-sm">明細 / Line Items</div>
+        <table class="w-full text-sm border-collapse">
+          <thead>
+            <tr class="text-left text-gray-500 border-b">
+              <th class="py-1">Category / 類別</th>
+              <th class="py-1">Description / 說明</th>
+              <th class="py-1 text-right">Amount / 金額</th>
+            </tr>
+          </thead>
+          <tbody>
+            <tr *ngFor="let line of expense.lines" class="border-b border-gray-100">
+              <td class="py-1">{{ line.categoryGroupName }}<span *ngIf="line.subCategoryName"> / {{ line.subCategoryName }}</span></td>
+              <td class="py-1 text-gray-600">{{ line.description || '—' }}</td>
+              <td class="py-1 text-right tabular-nums">{{ line.amount | currency }}</td>
+            </tr>
+          </tbody>
+          <tfoot>
+            <tr class="font-semibold">
+              <td class="py-1" colspan="2">Total / 合計</td>
+              <td class="py-1 text-right tabular-nums">{{ expense.amount | currency }}</td>
+            </tr>
+          </tfoot>
+        </table>
+      </div>
+
+      <!-- Reject reason capture (shown after clicking Reject) -->
+      <div *ngIf="rejecting" class="flex flex-col gap-2 rounded border border-red-200 bg-red-50 p-3">
+        <label class="flex flex-col gap-1 text-sm">Reject Reason / 拒絕原因
+          <kendo-dropdownlist [data]="rejectReasons" textField="label" valueField="value" [valuePrimitive]="true"
+            [(ngModel)]="rejectReason" [defaultItem]="{ value: null, label: '-- Select reason --/請選擇原因' }">
+          </kendo-dropdownlist>
+        </label>
+        <label *ngIf="isOtherReason" class="flex flex-col gap-1 text-sm">Detail / 說明
+          <kendo-textbox [(ngModel)]="rejectOther" placeholder="Please enter the reason / 請輸入原因"></kendo-textbox>
+        </label>
+      </div>
+    </div>
+
+    <!-- Right: receipt preview -->
+    <div class="md:w-[30rem] md:shrink-0 md:border-l md:pl-4 flex flex-col gap-2">
+      <div class="flex items-center justify-between">
+        <span class="font-semibold">收據預覽 / Receipt</span>
+        <div *ngIf="receiptImageUrl" class="flex items-center gap-1">
+          <button kendoButton size="small" fillMode="flat" (click)="zoomOut()"
+            [disabled]="receiptZoom <= minZoom" title="縮小 / Zoom out">−</button>
+          <span class="w-12 text-center text-sm tabular-nums">{{ receiptZoom * 100 | number:'1.0-0' }}%</span>
+          <button kendoButton size="small" fillMode="flat" (click)="zoomIn()"
+            [disabled]="receiptZoom >= maxZoom" title="放大 / Zoom in">＋</button>
+          <button kendoButton size="small" fillMode="flat" (click)="resetZoom()" title="重設 / Reset">⟲</button>
+        </div>
+      </div>
+
+      <div *ngIf="receiptImageUrl" class="overflow-auto rounded border border-gray-200 bg-gray-50" style="max-height: 72vh;">
+        <img [src]="receiptImageUrl" alt="Receipt preview" [style.width.%]="receiptZoom * 100" class="block max-w-none" />
+      </div>
+      <iframe *ngIf="receiptPdfUrl" [src]="receiptPdfUrl" title="Receipt PDF"
+        class="w-full rounded border border-gray-200" style="height: 72vh;"></iframe>
+
+      <div *ngIf="!showReceiptPanel" class="rounded border border-dashed border-gray-300 p-6 text-center text-gray-400 text-sm">
+        No receipt attached / 無收據
+      </div>
+    </div>
+
+  </div>
+
+  <kendo-dialog-actions>
+    <!-- Decision row -->
+    <ng-container *ngIf="!rejecting">
+      <button kendoButton (click)="cancel.emit()">Cancel / 取消</button>
+      <button kendoButton themeColor="error" fillMode="flat" (click)="startReject()">Reject / 拒絕</button>
+      <button kendoButton themeColor="success" (click)="confirmApprove()">Approve / 核准</button>
+    </ng-container>
+    <!-- Reject confirmation row -->
+    <ng-container *ngIf="rejecting">
+      <button kendoButton (click)="cancelReject()">Back / 返回</button>
+      <button kendoButton themeColor="error" [disabled]="!canConfirmReject" (click)="confirmReject()">Confirm Reject / 確認拒絕</button>
+    </ng-container>
+  </kendo-dialog-actions>
+</kendo-dialog>

APP/src/app/features/expense/components/expense-review-dialog/expense-review-dialog.component.ts

@@ -0,0 +1,106 @@
+import { Component, EventEmitter, Input, OnDestroy, OnInit, Output } from '@angular/core';
+import { CommonModule } from '@angular/common';
+import { FormsModule } from '@angular/forms';
+import { DomSanitizer, SafeResourceUrl } from '@angular/platform-browser';
+import { ButtonsModule } from '@progress/kendo-angular-buttons';
+import { DialogsModule } from '@progress/kendo-angular-dialog';
+import { DropDownsModule } from '@progress/kendo-angular-dropdowns';
+import { InputsModule } from '@progress/kendo-angular-inputs';
+import { ExpenseApiService } from '../../services/expense-api.service';
+import { ExpenseDto } from '../../models/expense.model';
+import { EXPENSE_REJECT_REASON_OPTIONS } from '../../../../shared/i18n/option-lists';
+
+/**
+ * Approval review dialog: shows the full expense detail and a receipt preview side by side,
+ * then lets a reviewer Approve or Reject (with a templated or free-text reason). The parent
+ * performs the actual api.approve / api.reject call from the emitted events.
+ */
+@Component({
+  selector: 'app-expense-review-dialog',
+  standalone: true,
+  imports: [CommonModule, FormsModule, ButtonsModule, DialogsModule, DropDownsModule, InputsModule],
+  templateUrl: './expense-review-dialog.component.html',
+})
+export class ExpenseReviewDialogComponent implements OnInit, OnDestroy {
+  /** Expense to review; the full detail (with lines) is fetched on open. */
+  @Input() expenseId!: number;
+  @Output() approve = new EventEmitter<void>();
+  @Output() reject = new EventEmitter<string>();   // emits the composed reviewNotes
+  @Output() cancel = new EventEmitter<void>();
+
+  expense: ExpenseDto | null = null;
+  loading = true;
+
+  readonly rejectReasons = EXPENSE_REJECT_REASON_OPTIONS;
+  /** false = the Approve/Reject choice; true = the reject reason is being collected. */
+  rejecting = false;
+  rejectReason: string | null = null;
+  rejectOther = '';
+
+  // ── Receipt preview (mirrors expense-form-dialog) ───────────────────────
+  receiptImageUrl: string | null = null;
+  receiptPdfUrl: SafeResourceUrl | null = null;
+  private receiptObjectUrl: string | null = null;
+  receiptZoom = 1;
+  readonly minZoom = 0.5;
+  readonly maxZoom = 5;
+
+  get showReceiptPanel(): boolean { return !!(this.receiptImageUrl || this.receiptPdfUrl); }
+
+  zoomIn(): void { this.receiptZoom = Math.min(this.maxZoom, +(this.receiptZoom + 0.25).toFixed(2)); }
+  zoomOut(): void { this.receiptZoom = Math.max(this.minZoom, +(this.receiptZoom - 0.25).toFixed(2)); }
+  resetZoom(): void { this.receiptZoom = 1; }
+
+  constructor(private api: ExpenseApiService, private sanitizer: DomSanitizer) {}
+
+  ngOnInit(): void {
+    this.api.getById(this.expenseId).subscribe({
+      next: dto => {
+        this.expense = dto;
+        this.loading = false;
+        if (dto.hasReceipt) {
+          this.api.downloadReceipt(dto.id).subscribe(blob => this.setPreview(blob, blob.type));
+        }
+      },
+      error: () => { this.loading = false; },
+    });
+  }
+
+  ngOnDestroy(): void { this.clearPreview(); }
+
+  private setPreview(blob: Blob, contentType: string): void {
+    this.clearPreview();
+    this.receiptZoom = 1;
+    this.receiptObjectUrl = URL.createObjectURL(blob);
+    if (contentType.startsWith('image/')) {
+      this.receiptImageUrl = this.receiptObjectUrl;
+    } else {
+      this.receiptPdfUrl = this.sanitizer.bypassSecurityTrustResourceUrl(this.receiptObjectUrl);
+    }
+  }
+
+  private clearPreview(): void {
+    if (this.receiptObjectUrl) { URL.revokeObjectURL(this.receiptObjectUrl); this.receiptObjectUrl = null; }
+    this.receiptImageUrl = null;
+    this.receiptPdfUrl = null;
+  }
+
+  startReject(): void { this.rejecting = true; this.rejectReason = null; this.rejectOther = ''; }
+  cancelReject(): void { this.rejecting = false; }
+
+  get isOtherReason(): boolean { return this.rejectReason === 'Other'; }
+
+  /** The reason text actually sent: the template value, or the free text when "Other" is chosen. */
+  get composedReviewNotes(): string {
+    return this.isOtherReason ? this.rejectOther.trim() : (this.rejectReason ?? '');
+  }
+
+  get canConfirmReject(): boolean { return this.composedReviewNotes.length > 0; }
+
+  confirmApprove(): void { this.approve.emit(); }
+
+  confirmReject(): void {
+    if (!this.canConfirmReject) return;
+    this.reject.emit(this.composedReviewNotes);
+  }
+}

APP/src/app/features/expense/models/expense-snapshot.model.ts

@@ -0,0 +1,21 @@
+import { ExpenseLineInput, FunctionalClass } from './expense.model';
+
+export interface ExpenseSnapshotLineDto {
+  categoryGroupId: number; categoryGroupName: string;
+  subCategoryId: number; subCategoryName: string;
+  functionalClass: FunctionalClass | null; amount: number; description: string | null;
+}
+
+export interface ExpenseSnapshotDto {
+  id: number; name: string; ministryId: number; ministryName: string;
+  description: string; vendorName: string | null; checkNumber: string | null; notes: string | null;
+  totalAmount: number; lineCount: number;
+  createdByName: string | null; createdAt: string;
+  lines: ExpenseSnapshotLineDto[];
+}
+
+export interface CreateExpenseSnapshotRequest {
+  name: string; ministryId: number; lines: ExpenseLineInput[];
+  description: string; vendorName: string | null; checkNumber: string | null; notes: string | null;
+}
+export type UpdateExpenseSnapshotRequest = CreateExpenseSnapshotRequest;

APP/src/app/features/expense/models/expense.model.ts

@@ -8,28 +8,70 @@ export interface PagedResult<T> {
 
 export interface MinistryDto { id: number; name_en: string; name_zh: string | null; sortOrder: number; isActive: boolean; label?: string; }
 
-export interface ExpenseSubCategoryDto { id: number; groupId: number; name_en: string; name_zh: string | null; sortOrder: number; isActive: boolean; label?: string; form990LineId: number | null; form990LineCode: string | null; }
+export interface ExpenseSubCategoryDto { id: number; groupId: number; name_en: string; name_zh: string | null; sortOrder: number; isActive: boolean; label?: string; form990LineId: number | null; form990LineCode: string | null; form1099BoxId: number | null; form1099BoxCode: string | null; }
-export interface ExpenseCategoryGroupDto { id: number; name_en: string; name_zh: string | null; sortOrder: number; isActive: boolean; subCategories: ExpenseSubCategoryDto[]; label?: string; form990LineId: number | null; form990LineCode: string | null; }
+export interface ExpenseCategoryGroupDto { id: number; name_en: string; name_zh: string | null; sortOrder: number; isActive: boolean; subCategories: ExpenseSubCategoryDto[]; label?: string; form990LineId: number | null; form990LineCode: string | null; form1099BoxId: number | null; form1099BoxCode: string | null; }
-export interface CreateExpenseGroupRequest { name_en: string; name_zh: string | null; sortOrder: number; form990LineId: number | null; }
+export interface CreateExpenseGroupRequest { name_en: string; name_zh: string | null; sortOrder: number; form990LineId: number | null; form1099BoxId: number | null; }
 export interface UpdateExpenseGroupRequest extends CreateExpenseGroupRequest { isActive: boolean; }
-export interface CreateExpenseSubCategoryRequest { groupId: number; name_en: string; name_zh: string | null; sortOrder: number; form990LineId: number | null; }
+export interface CreateExpenseSubCategoryRequest { groupId: number; name_en: string; name_zh: string | null; sortOrder: number; form990LineId: number | null; form1099BoxId: number | null; }
 export interface UpdateExpenseSubCategoryRequest extends CreateExpenseSubCategoryRequest { isActive: boolean; }
 
+export interface ExpenseLineItemDto {
+  id: number; categoryGroupId: number; categoryGroupName: string;
+  subCategoryId: number; subCategoryName: string;
+  functionalClass: FunctionalClass | null; amount: number; description: string | null;
+}
 export interface ExpenseListItemDto {
   id: number; type: ExpenseType; status: ExpenseStatus; amount: number; description: string;
-  ministryId: number; ministryName: string; categoryGroupId: number; categoryGroupName: string;
+  ministryId: number; ministryName: string; lineCount: number; primaryCategoryName: string;
-  subCategoryId: number; subCategoryName: string; vendorName: string | null;
+  vendorName: string | null;
-  memberId: number | null; memberName: string | null; expenseDate: string; hasReceipt: boolean;
+  memberId: number | null; memberName: string | null; memberNickName: string | null;
-  checkNumber: string | null; functionalClass: FunctionalClass | null;
+  expenseDate: string; hasReceipt: boolean;
+  checkNumber: string | null;
+  reviewedByName: string | null; reviewedAt: string | null; reviewNotes: string | null;
+  payeeId: number | null;
 }
 export interface ExpenseDto extends ExpenseListItemDto {
-  notes: string | null; reviewNotes: string | null;
+  notes: string | null;
-  submittedBy: string | null; submittedAt: string | null; reviewedAt: string | null; paidAt: string | null;
+  submittedBy: string | null; submittedAt: string | null; paidAt: string | null;
+  lines: ExpenseLineItemDto[];
+}
+/** AI assist suggestion: English translation + a proposed major/sub category (null when unclassified). */
+export interface ExpenseAiSuggestion {
+  englishDescription: string | null;
+  chineseDescription: string | null;
+  groupId: number | null;
+  subCategoryId: number | null;
+  groupLabel: string | null;
+  subLabel: string | null;
+  confidence: number;
+}
+
+/** Request to AI-assist defining an expense category (大項/小項). */
+export interface ExpenseCategoryAiRequest {
+  name_zh: string;
+  name_en?: string | null;
+  level: 'group' | 'sub';
+  parentGroupName?: string | null;
+  parentForm990LineId?: number | null;
+}
+/** AI suggestion for a category: refined Chinese name, English translation, and a Form 990 line. */
+export interface CategoryAiSuggestion {
+  chineseName: string | null;
+  englishName: string | null;
+  form990LineId: number | null;
+  form990LineLabel: string | null;
+  confidence: number;
+}
+
+export interface ExpenseLineInput {
+  categoryGroupId: number; subCategoryId: number; amount: number;
+  functionalClass: FunctionalClass | null; description: string | null;
 }
 export interface CreateExpenseRequest {
-  type: ExpenseType; ministryId: number; categoryGroupId: number; subCategoryId: number;
+  type: ExpenseType; ministryId: number; lines: ExpenseLineInput[];
-  amount: number; description: string; vendorName: string | null; memberId: number | null;
+  description: string; vendorName: string | null; memberId: number | null;
-  checkNumber: string | null; expenseDate: string; notes: string | null; functionalClass: FunctionalClass | null;
+  checkNumber: string | null; expenseDate: string; notes: string | null;
+  payeeId: number | null;
 }
 export type UpdateExpenseRequest = CreateExpenseRequest;
 export interface RejectExpenseRequest { reviewNotes: string | null; }

APP/src/app/features/expense/pages/expense-categories-page/expense-categories-page.component.html

@@ -53,15 +53,45 @@
         Name (EN) *
         <kendo-textbox [(ngModel)]="groupForm.name_en"></kendo-textbox>
       </label>
-      <label class="flex flex-col gap-1">
+      <!-- Chinese name with AI assist: refine 中文 + translate to English + suggest a 990 line -->
-        名稱 (中)
+      <div class="flex flex-col gap-1 md:col-span-2">
-        <kendo-textbox [(ngModel)]="groupForm.name_zh"></kendo-textbox>
+        <div class="flex items-end justify-between gap-2">
+          <label class="flex flex-1 flex-col gap-1">名稱 (中)
+            <kendo-textbox [(ngModel)]="groupForm.name_zh" placeholder="可輸入中文，AI 幫忙翻譯"></kendo-textbox>
           </label>
+          <button kendoButton fillMode="outline" themeColor="primary" type="button"
+            [disabled]="(!groupForm.name_zh.trim() && !groupForm.name_en.trim()) || groupAiLoading"
+            (click)="requestGroupAiSuggest()"
+            title="翻譯英文並建議 990 Line / Translate + suggest 990 line">
+            {{ groupAiLoading ? '思考中… / Thinking…' : '✨ AI 建議' }}
+          </button>
+        </div>
+        <div *ngIf="groupAiSuggestion" class="rounded border border-blue-200 bg-blue-50 p-3 flex flex-col gap-2 text-sm">
+          <div class="font-semibold text-blue-800">AI 建議 / Suggestion</div>
+          <div *ngIf="groupAiSuggestion.englishName" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">English:</span>
+            <span class="font-medium">{{ groupAiSuggestion.englishName }}</span>
+          </div>
+          <div *ngIf="groupAiSuggestion.chineseName" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">中文:</span>
+            <span class="font-medium">{{ groupAiSuggestion.chineseName }}</span>
+          </div>
+          <div *ngIf="groupAiSuggestion.form990LineLabel" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">990 Line:</span>
+            <span class="font-medium">{{ groupAiSuggestion.form990LineLabel }}</span>
+          </div>
+          <div class="text-xs text-gray-500">信心 / Confidence: {{ groupAiSuggestion.confidence * 100 | number:'1.0-0' }}%</div>
+          <div class="flex gap-2">
+            <button kendoButton themeColor="primary" size="small" type="button" (click)="applyGroupAiSuggestion()">套用 / Apply</button>
+            <button kendoButton fillMode="flat" size="small" type="button" (click)="dismissGroupAiSuggestion()">忽略 / Dismiss</button>
+          </div>
+        </div>
+      </div>
       <label class="flex flex-col gap-1">
         Sort order
         <kendo-numerictextbox [(ngModel)]="groupForm.sortOrder" [format]="'n0'" [decimals]="0" [min]="0"></kendo-numerictextbox>
       </label>
-      <label class="flex flex-col gap-1 md:col-span-2">
+      <label class="flex flex-col gap-1">
         <span>Form 990 Line / 990 行</span>
         <kendo-dropdownlist
           [data]="form990Lines"
@@ -70,6 +100,15 @@
           [(ngModel)]="groupForm.form990LineId">
         </kendo-dropdownlist>
       </label>
+      <label class="flex flex-col gap-1">
+        <span>1099 Box / 1099 框</span>
+        <kendo-dropdownlist
+          [data]="form1099Boxes"
+          textField="label" valueField="id" [valuePrimitive]="true"
+          [defaultItem]="{ id: null, label: '— none —' }"
+          [(ngModel)]="groupForm.form1099BoxId">
+        </kendo-dropdownlist>
+      </label>
       <label *ngIf="editingGroupId != null" class="flex items-center gap-2 md:col-span-2">
         <input type="checkbox" [(ngModel)]="groupForm.isActive" /> Active
       </label>
@@ -90,15 +129,45 @@
         Name (EN) *
         <kendo-textbox [(ngModel)]="subForm.name_en"></kendo-textbox>
       </label>
-      <label class="flex flex-col gap-1">
+      <!-- Chinese name with AI assist: refine 中文 + translate to English + suggest a 990 line (biased by parent group) -->
-        名稱 (中)
+      <div class="flex flex-col gap-1 md:col-span-2">
-        <kendo-textbox [(ngModel)]="subForm.name_zh"></kendo-textbox>
+        <div class="flex items-end justify-between gap-2">
+          <label class="flex flex-1 flex-col gap-1">名稱 (中)
+            <kendo-textbox [(ngModel)]="subForm.name_zh" placeholder="可輸入中文，AI 幫忙翻譯"></kendo-textbox>
           </label>
+          <button kendoButton fillMode="outline" themeColor="primary" type="button"
+            [disabled]="(!subForm.name_zh.trim() && !subForm.name_en.trim()) || subAiLoading"
+            (click)="requestSubAiSuggest()"
+            title="翻譯英文並建議 990 Line / Translate + suggest 990 line">
+            {{ subAiLoading ? '思考中… / Thinking…' : '✨ AI 建議' }}
+          </button>
+        </div>
+        <div *ngIf="subAiSuggestion" class="rounded border border-blue-200 bg-blue-50 p-3 flex flex-col gap-2 text-sm">
+          <div class="font-semibold text-blue-800">AI 建議 / Suggestion</div>
+          <div *ngIf="subAiSuggestion.englishName" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">English:</span>
+            <span class="font-medium">{{ subAiSuggestion.englishName }}</span>
+          </div>
+          <div *ngIf="subAiSuggestion.chineseName" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">中文:</span>
+            <span class="font-medium">{{ subAiSuggestion.chineseName }}</span>
+          </div>
+          <div *ngIf="subAiSuggestion.form990LineLabel" class="flex gap-2">
+            <span class="text-gray-500 shrink-0">990 Line:</span>
+            <span class="font-medium">{{ subAiSuggestion.form990LineLabel }}</span>
+          </div>
+          <div class="text-xs text-gray-500">信心 / Confidence: {{ subAiSuggestion.confidence * 100 | number:'1.0-0' }}%</div>
+          <div class="flex gap-2">
+            <button kendoButton themeColor="primary" size="small" type="button" (click)="applySubAiSuggestion()">套用 / Apply</button>
+            <button kendoButton fillMode="flat" size="small" type="button" (click)="dismissSubAiSuggestion()">忽略 / Dismiss</button>
+          </div>
+        </div>
+      </div>
       <label class="flex flex-col gap-1">
         Sort order
         <kendo-numerictextbox [(ngModel)]="subForm.sortOrder" [format]="'n0'" [decimals]="0" [min]="0"></kendo-numerictextbox>
       </label>
-      <label class="flex flex-col gap-1 md:col-span-2">
+      <label class="flex flex-col gap-1">
         <span>Form 990 Line / 990 行</span>
         <kendo-dropdownlist
           [data]="form990Lines"
@@ -107,6 +176,15 @@
           [(ngModel)]="subForm.form990LineId">
         </kendo-dropdownlist>
       </label>
+      <label class="flex flex-col gap-1">
+        <span>1099 Box / 1099 框</span>
+        <kendo-dropdownlist
+          [data]="form1099Boxes"
+          textField="label" valueField="id" [valuePrimitive]="true"
+          [defaultItem]="{ id: null, label: '— none —' }"
+          [(ngModel)]="subForm.form1099BoxId">
+        </kendo-dropdownlist>
+      </label>
       <label *ngIf="editingSubId != null" class="flex items-center gap-2 md:col-span-2">
         <input type="checkbox" [(ngModel)]="subForm.isActive" /> Active
       </label>

APP/src/app/features/expense/pages/expense-categories-page/expense-categories-page.component.ts

@@ -8,8 +8,9 @@ import { InputsModule } from '@progress/kendo-angular-inputs';
 import { DropDownsModule } from '@progress/kendo-angular-dropdowns';
 import { ContextMenuModule, ContextMenuComponent, ContextMenuSelectEvent } from '@progress/kendo-angular-menu';
 import { ExpenseCategoryApiService } from '../../services/expense-category-api.service';
-import { ExpenseCategoryGroupDto, ExpenseSubCategoryDto } from '../../models/expense.model';
+import { ExpenseCategoryGroupDto, ExpenseSubCategoryDto, CategoryAiSuggestion } from '../../models/expense.model';
 import { Form990ExpenseLineDto } from '../../../finance-report/models/form990-report.model';
+import { Form1099Box } from '../../../payee1099/models/payee1099.model';
 
 @Component({
   selector: 'app-expense-categories-page',
@@ -23,6 +24,7 @@ export class ExpenseCategoriesPageComponent implements OnInit {
   selectedGroup: ExpenseCategoryGroupDto | null = null;
   loading = false;
   form990Lines: Form990ExpenseLineDto[] = [];
+  form1099Boxes: (Form1099Box & { label: string })[] = [];
 
   @ViewChild('groupMenu') groupMenu!: ContextMenuComponent;
   @ViewChild('subMenu') subMenu!: ContextMenuComponent;
@@ -33,17 +35,22 @@ export class ExpenseCategoriesPageComponent implements OnInit {
 
   groupDialogOpen = false;
   editingGroupId: number | null = null;
-  groupForm = { name_en: '', name_zh: '', sortOrder: 0, isActive: true, form990LineId: null as number | null };
+  groupForm = { name_en: '', name_zh: '', sortOrder: 0, isActive: true, form990LineId: null as number | null, form1099BoxId: null as number | null };
+  groupAiLoading = false;
+  groupAiSuggestion: CategoryAiSuggestion | null = null;
 
   subDialogOpen = false;
   editingSubId: number | null = null;
-  subForm = { name_en: '', name_zh: '', sortOrder: 0, isActive: true, form990LineId: null as number | null };
+  subForm = { name_en: '', name_zh: '', sortOrder: 0, isActive: true, form990LineId: null as number | null, form1099BoxId: null as number | null };
+  subAiLoading = false;
+  subAiSuggestion: CategoryAiSuggestion | null = null;
 
   constructor(private api: ExpenseCategoryApiService) {}
 
   ngOnInit(): void {
     this.load();
     this.api.getForm990Lines().subscribe(lines => { this.form990Lines = lines; });
+    this.api.getForm1099Boxes().subscribe(boxes => { this.form1099Boxes = boxes; });
   }
 
   load(): void {
@@ -107,16 +114,39 @@ export class ExpenseCategoriesPageComponent implements OnInit {
 
   openNewGroup(): void {
     this.editingGroupId = null;
-    this.groupForm = { name_en: '', name_zh: '', sortOrder: this.groups.length + 1, isActive: true, form990LineId: null };
+    this.groupForm = { name_en: '', name_zh: '', sortOrder: this.groups.length + 1, isActive: true, form990LineId: null, form1099BoxId: null };
+    this.resetGroupAi();
     this.groupDialogOpen = true;
   }
   openEditGroup(g: ExpenseCategoryGroupDto): void {
     this.editingGroupId = g.id;
-    this.groupForm = { name_en: g.name_en, name_zh: g.name_zh ?? '', sortOrder: g.sortOrder, isActive: g.isActive, form990LineId: g.form990LineId };
+    this.groupForm = { name_en: g.name_en, name_zh: g.name_zh ?? '', sortOrder: g.sortOrder, isActive: g.isActive, form990LineId: g.form990LineId, form1099BoxId: g.form1099BoxId };
+    this.resetGroupAi();
     this.groupDialogOpen = true;
   }
+
+  // ── Group AI assist: refine the Chinese name, translate to English, suggest a Form 990 line ──
+  private resetGroupAi(): void { this.groupAiLoading = false; this.groupAiSuggestion = null; }
+  requestGroupAiSuggest(): void {
+    if (this.groupAiLoading) return;
+    this.groupAiLoading = true;
+    this.groupAiSuggestion = null;
+    this.api.aiSuggest({ name_zh: this.groupForm.name_zh.trim(), name_en: this.groupForm.name_en.trim() || null, level: 'group' }).subscribe({
+      next: s => { this.groupAiSuggestion = s; this.groupAiLoading = false; },
+      error: () => { this.groupAiLoading = false; },
+    });
+  }
+  applyGroupAiSuggestion(): void {
+    const s = this.groupAiSuggestion;
+    if (!s) return;
+    if (s.chineseName) this.groupForm.name_zh = s.chineseName;
+    if (s.englishName) this.groupForm.name_en = s.englishName;
+    if (s.form990LineId != null) this.groupForm.form990LineId = s.form990LineId;
+    this.groupAiSuggestion = null;
+  }
+  dismissGroupAiSuggestion(): void { this.groupAiSuggestion = null; }
   saveGroup(): void {
-    const body = { name_en: this.groupForm.name_en, name_zh: this.groupForm.name_zh || null, sortOrder: this.groupForm.sortOrder, form990LineId: this.groupForm.form990LineId };
+    const body = { name_en: this.groupForm.name_en, name_zh: this.groupForm.name_zh || null, sortOrder: this.groupForm.sortOrder, form990LineId: this.groupForm.form990LineId, form1099BoxId: this.groupForm.form1099BoxId };
     const done = () => { this.groupDialogOpen = false; this.load(); };
     if (this.editingGroupId == null) this.api.createGroup(body).subscribe(done);
     else this.api.updateGroup(this.editingGroupId, { ...body, isActive: this.groupForm.isActive }).subscribe(done);
@@ -129,17 +159,46 @@ export class ExpenseCategoriesPageComponent implements OnInit {
   openNewSub(): void {
     if (!this.selectedGroup) return;
     this.editingSubId = null;
-    this.subForm = { name_en: '', name_zh: '', sortOrder: this.subCategories.length + 1, isActive: true, form990LineId: null };
+    this.subForm = { name_en: '', name_zh: '', sortOrder: this.subCategories.length + 1, isActive: true, form990LineId: null, form1099BoxId: null };
+    this.resetSubAi();
     this.subDialogOpen = true;
   }
   openEditSub(s: ExpenseSubCategoryDto): void {
     this.editingSubId = s.id;
-    this.subForm = { name_en: s.name_en, name_zh: s.name_zh ?? '', sortOrder: s.sortOrder, isActive: s.isActive, form990LineId: s.form990LineId };
+    this.subForm = { name_en: s.name_en, name_zh: s.name_zh ?? '', sortOrder: s.sortOrder, isActive: s.isActive, form990LineId: s.form990LineId, form1099BoxId: s.form1099BoxId };
+    this.resetSubAi();
     this.subDialogOpen = true;
   }
+
+  // ── Subcategory AI assist: same as group, biased by the selected parent group + its 990 line ──
+  private resetSubAi(): void { this.subAiLoading = false; this.subAiSuggestion = null; }
+  requestSubAiSuggest(): void {
+    if (this.subAiLoading || !this.selectedGroup) return;
+    this.subAiLoading = true;
+    this.subAiSuggestion = null;
+    this.api.aiSuggest({
+      name_zh: this.subForm.name_zh.trim(),
+      name_en: this.subForm.name_en.trim() || null,
+      level: 'sub',
+      parentGroupName: this.selectedGroup.label ?? this.selectedGroup.name_en,
+      parentForm990LineId: this.selectedGroup.form990LineId,
+    }).subscribe({
+      next: s => { this.subAiSuggestion = s; this.subAiLoading = false; },
+      error: () => { this.subAiLoading = false; },
+    });
+  }
+  applySubAiSuggestion(): void {
+    const s = this.subAiSuggestion;
+    if (!s) return;
+    if (s.chineseName) this.subForm.name_zh = s.chineseName;
+    if (s.englishName) this.subForm.name_en = s.englishName;
+    if (s.form990LineId != null) this.subForm.form990LineId = s.form990LineId;
+    this.subAiSuggestion = null;
+  }
+  dismissSubAiSuggestion(): void { this.subAiSuggestion = null; }
   saveSub(): void {
     if (!this.selectedGroup) return;
-    const body = { groupId: this.selectedGroup.id, name_en: this.subForm.name_en, name_zh: this.subForm.name_zh || null, sortOrder: this.subForm.sortOrder, form990LineId: this.subForm.form990LineId };
+    const body = { groupId: this.selectedGroup.id, name_en: this.subForm.name_en, name_zh: this.subForm.name_zh || null, sortOrder: this.subForm.sortOrder, form990LineId: this.subForm.form990LineId, form1099BoxId: this.subForm.form1099BoxId };
     const done = () => { this.subDialogOpen = false; this.load(); };
     if (this.editingSubId == null) this.api.createSub(body).subscribe(done);
     else this.api.updateSub(this.editingSubId, { ...body, isActive: this.subForm.isActive }).subscribe(done);

APP/src/app/features/expense/pages/expense-snapshots-page/expense-snapshots-page.component.html

@@ -0,0 +1,68 @@
+<div class="page">
+  <p class="mb-4 text-sm text-gray-600">
+    儲存常用的固定費用（房租、網路、餐費…）為範本，下次可快速套用。費用日期不會儲存。<br>
+    Save recurring fixed expenses as snapshots to quickly re-use them. The Expense Date is never saved.
+  </p>
+
+  <!-- Desktop: grid -->
+  <div class="hidden md:block">
+    <kendo-grid [data]="rows" [loading]="loading">
+      <kendo-grid-column field="name" title="Snapshot / 範本" [width]="240"></kendo-grid-column>
+      <kendo-grid-column field="vendorName" title="Vendor / 廠商" [width]="180">
+        <ng-template kendoGridCellTemplate let-dataItem>{{ dataItem.vendorName || '—' }}</ng-template>
+      </kendo-grid-column>
+      <kendo-grid-column field="ministryName" title="Ministry / 事工"></kendo-grid-column>
+      <kendo-grid-column field="totalAmount" title="Amount / 金額" [width]="120" format="c2"></kendo-grid-column>
+      <kendo-grid-column title="Created by / 建立者" [width]="200">
+        <ng-template kendoGridCellTemplate let-dataItem>
+          {{ dataItem.createdByName || '—' }}<br>
+          <span class="text-xs text-gray-500">{{ dataItem.createdAt | date:'yyyy-MM-dd' }}</span>
+        </ng-template>
+      </kendo-grid-column>
+      <kendo-grid-column title="Actions" [width]="160">
+        <ng-template kendoGridCellTemplate let-dataItem>
+          <button kendoButton fillMode="flat" (click)="openRename(dataItem)">Rename</button>
+          <button kendoButton fillMode="flat" themeColor="error" (click)="openDelete(dataItem)">Delete</button>
+        </ng-template>
+      </kendo-grid-column>
+    </kendo-grid>
+  </div>
+
+  <!-- Mobile: card list -->
+  <div class="md:hidden flex flex-col gap-3">
+    <div *ngFor="let row of rows" class="rounded border border-gray-200 p-3 flex flex-col gap-1">
+      <div class="flex items-center justify-between">
+        <span class="font-semibold">{{ row.name }}</span>
+        <span class="tabular-nums">{{ row.totalAmount | currency }}</span>
+      </div>
+      <div class="text-sm text-gray-600">{{ row.vendorName || '—' }} · {{ row.ministryName }}</div>
+      <div class="text-xs text-gray-500">{{ row.createdByName || '—' }} · {{ row.createdAt | date:'yyyy-MM-dd' }}</div>
+      <div class="flex gap-2 pt-1">
+        <button kendoButton size="small" fillMode="outline" (click)="openRename(row)">Rename</button>
+        <button kendoButton size="small" fillMode="outline" themeColor="error" (click)="openDelete(row)">Delete</button>
+      </div>
+    </div>
+    <p *ngIf="!loading && rows.length === 0" class="text-sm text-gray-500">尚無範本 / No snapshots yet.</p>
+  </div>
+
+  <!-- Rename dialog -->
+  <kendo-dialog *ngIf="renameRow" title="重新命名 / Rename Snapshot" [width]="420" [maxWidth]="'95vw'" (close)="cancelRename()">
+    <label class="flex flex-col gap-1 p-2">名稱 / Name
+      <kendo-textbox [(ngModel)]="renameValue"></kendo-textbox>
+    </label>
+    <kendo-dialog-actions>
+      <button kendoButton (click)="cancelRename()">Cancel</button>
+      <button kendoButton themeColor="primary" [disabled]="!renameValue.trim() || renameSaving"
+        (click)="confirmRename()">{{ renameSaving ? 'Saving…' : 'Save' }}</button>
+    </kendo-dialog-actions>
+  </kendo-dialog>
+
+  <!-- Delete confirm dialog -->
+  <kendo-dialog *ngIf="deleteRow" title="刪除 / Delete Snapshot" [width]="420" [maxWidth]="'95vw'" (close)="cancelDelete()">
+    <p class="p-2">確定刪除「{{ deleteRow.name }}」？ / Delete "{{ deleteRow.name }}"?</p>
+    <kendo-dialog-actions>
+      <button kendoButton (click)="cancelDelete()">Cancel</button>
+      <button kendoButton themeColor="error" (click)="confirmDelete()">Delete</button>
+    </kendo-dialog-actions>
+  </kendo-dialog>
+</div>

APP/src/app/features/expense/pages/expense-snapshots-page/expense-snapshots-page.component.scss

@@ -0,0 +1,3 @@
+.page {
+  padding: 0.5rem 0;
+}