fix(jobs): derive attachment checklist flags from actual Attachments

Backlog item 4 (Wave 3, first sub-item). HasResume/HasCoverLetter/HasPortfolio/
HasOtherAttachment were manually-editable checkboxes in EditJobDialog,
completely independent of whether a file was actually attached -- classic
drift: mark 'resume ready' by hand, later delete the resume attachment, flag
stays stuck true forever. User confirmed (asked directly, since removing the
manual-override capability is a product decision, not purely technical):
make them fully computed from Attachments, no manual override.

- AttachmentsController.RecomputeAttachmentFlagsAsync: the single place these
  four fields get written now, called after every attachment mutation
  (upload, delete, Purpose change) that could affect them. Deliberately kept
  as persisted columns (not [NotMapped] computed properties reading the
  Attachments navigation collection) -- ~15 query sites build JobApplication
  DTOs without .Include(Attachments), so a live-computed property would
  silently return false everywhere instead of throwing, the worst kind of
  bug. Recomputing at the one write funnel avoids touching any read path.
- Removed HasResume/etc from CreateJobApplicationRequest/
  UpdateJobApplicationRequest -- no longer client-settable.
- EditJobDialog: removed the manual checkboxes, kept the (now genuinely
  accurate) read-only status chips.
- AddJobModal: stopped sending has*-flags at job-creation time; the
  follow-up attachment upload call now sets them correctly via the same
  recompute path.

Caught a real bug while testing this: the Purpose-change path recomputed
before saving the Purpose change, so a fresh query missed the pending edit
and the flags never updated. Fixed by committing the mutation before
recomputing.

3 new backend tests (purpose-change sets flag, delete clears flag,
non-primary purpose counts as "other"). 172/172 backend, 25/25 frontend
suites (57 tests) green.

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

JobTrackerApi.Tests/AttachmentFlagsRecomputeTests.cs

@@ -0,0 +1,111 @@
+using JobTrackerApi.Controllers;
+using JobTrackerApi.Data;
+using JobTrackerApi.Models;
+using JobTrackerApi.Services;
+using JobTrackerApi.Tests.TestSupport;
+using Microsoft.EntityFrameworkCore;
+using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.Hosting;
+using Microsoft.AspNetCore.Http;
+using Microsoft.AspNetCore.Mvc;
+using Moq;
+using Xunit;
+
+namespace JobTrackerApi.Tests;
+
+// JobApplication.HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
+// Attachment rows (backlog Wave 3), not manually settable. These tests exercise the single
+// place they're written: AttachmentsController's Purpose-change and Delete paths.
+public sealed class AttachmentFlagsRecomputeTests
+{
+    [Fact]
+    public async Task Changing_purpose_to_resume_sets_HasResume()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "other");
+        var controller = CreateController(db);
+
+        var result = await controller.Rename(attachment.Id, new AttachmentsController.UpdateAttachmentRequest(null, "resume", null), CancellationToken.None);
+
+        Assert.IsType<NoContentResult>(result);
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.True(updated.HasResume);
+        Assert.True(updated.HasOtherAttachment == false);
+    }
+
+    [Fact]
+    public async Task Deleting_the_only_resume_attachment_clears_HasResume()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "resume");
+        var controller = CreateController(db);
+
+        var result = await controller.Delete(attachment.Id, CancellationToken.None);
+
+        Assert.IsType<NoContentResult>(result);
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.False(updated.HasResume);
+    }
+
+    [Fact]
+    public async Task Attachment_with_case_study_purpose_counts_as_other()
+    {
+        await using var db = TestHostFactory.CreateInMemoryDb();
+        var (job, attachment) = await SeedJobWithAttachmentAsync(db, purpose: "resume");
+        var controller = CreateController(db);
+
+        await controller.Rename(attachment.Id, new AttachmentsController.UpdateAttachmentRequest(null, "case-study", null), CancellationToken.None);
+
+        var updated = await db.JobApplications.SingleAsync(j => j.Id == job.Id);
+        Assert.False(updated.HasResume);
+        Assert.True(updated.HasOtherAttachment);
+    }
+
+    private static async Task<(JobApplication Job, Attachment Attachment)> SeedJobWithAttachmentAsync(JobTrackerContext db, string purpose)
+    {
+        var company = new Company { Name = "Acme", OwnerUserId = "user-1" };
+        db.Companies.Add(company);
+        await db.SaveChangesAsync();
+
+        var job = new JobApplication { JobTitle = "Backend Developer", CompanyId = company.Id, OwnerUserId = "user-1" };
+        db.JobApplications.Add(job);
+        await db.SaveChangesAsync();
+
+        var attachment = new Attachment
+        {
+            JobApplicationId = job.Id,
+            FileName = "file.pdf",
+            FilePath = Path.Combine(Path.GetTempPath(), $"jobtracker-attachment-test-{Guid.NewGuid():N}.pdf"),
+            FileType = "application/pdf",
+            FileSize = 100,
+            Purpose = purpose,
+        };
+        db.Attachments.Add(attachment);
+        await db.SaveChangesAsync();
+
+        job.HasResume = purpose == "resume";
+        job.HasOtherAttachment = purpose is not ("resume" or "cover-letter" or "portfolio");
+        await db.SaveChangesAsync();
+
+        return (job, attachment);
+    }
+
+    private static AttachmentsController CreateController(JobTrackerContext db)
+    {
+        var tempRoot = Path.Combine(Path.GetTempPath(), $"jobtracker-attachments-tests-{Guid.NewGuid():N}");
+        Directory.CreateDirectory(tempRoot);
+
+        var config = new ConfigurationBuilder()
+            .AddInMemoryCollection(new Dictionary<string, string?> { ["Data:Root"] = tempRoot })
+            .Build();
+
+        var env = new Mock<IHostEnvironment>();
+        env.SetupGet(x => x.ContentRootPath).Returns(tempRoot);
+        var paths = new AppPaths(config, env.Object);
+
+        return new AttachmentsController(paths, db)
+        {
+            ControllerContext = new ControllerContext { HttpContext = new DefaultHttpContext() }
+        };
+    }
+}

JobTrackerApi.Tests/JobApplicationsEndpointBehaviorTests.cs

@@ -202,11 +202,7 @@ public sealed class JobApplicationsEndpointBehaviorTests
             CoverLetterText: null,
             JobUrl: null,
             DateApplied: null,
-            FeedbackRequestedAt: null,
+            FeedbackRequestedAt: null);
-            HasResume: null,
-            HasCoverLetter: null,
-            HasPortfolio: null,
-            HasOtherAttachment: null);
 
         var result = await controller.Create(request, CancellationToken.None);
 
@@ -255,10 +251,6 @@ public sealed class JobApplicationsEndpointBehaviorTests
             SalaryPeriod: "fortnight",
             NextAction: null,
             FollowUpAt: null,
-            HasResume: null,
-            HasCoverLetter: null,
-            HasPortfolio: null,
-            HasOtherAttachment: null,
             Notes: null,
             Description: null,
             TranslatedDescription: null,

JobTrackerApi/Controllers/AttachmentsController.cs

@@ -59,6 +59,26 @@ namespace JobTrackerApi.Controllers
             return "other";
         }
 
+        // JobApplication.HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived
+        // from actual Attachment rows, not manually settable -- this is the single place they're
+        // written, called after every attachment mutation (upload/delete/purpose change) so they
+        // can never drift from what's actually attached.
+        private async Task RecomputeAttachmentFlagsAsync(int jobId, CancellationToken cancellationToken)
+        {
+            var job = await _db.JobApplications.FirstOrDefaultAsync(j => j.Id == jobId, cancellationToken);
+            if (job is null) return;
+
+            var purposes = await _db.Attachments
+                .Where(a => a.JobApplicationId == jobId)
+                .Select(a => a.Purpose)
+                .ToListAsync(cancellationToken);
+
+            job.HasResume = purposes.Any(p => p == "resume");
+            job.HasCoverLetter = purposes.Any(p => p == "cover-letter");
+            job.HasPortfolio = purposes.Any(p => p == "portfolio");
+            job.HasOtherAttachment = purposes.Any(p => p is not ("resume" or "cover-letter" or "portfolio"));
+        }
+
         [HttpGet("{jobId:int}")]
         public async Task<ActionResult<List<AttachmentDto>>> ListForJob([FromRoute] int jobId, CancellationToken cancellationToken)
         {
@@ -102,15 +122,23 @@ namespace JobTrackerApi.Controllers
                 att.UseForAi = request.UseForAi.Value;
             }
 
-            if (!string.IsNullOrWhiteSpace(request.Purpose))
+            var purposeChanged = !string.IsNullOrWhiteSpace(request.Purpose);
+            if (purposeChanged)
             {
-                att.Purpose = request.Purpose.Trim().ToLowerInvariant();
+                att.Purpose = request.Purpose!.Trim().ToLowerInvariant();
             }
 
             var rawName = (request.FileName ?? string.Empty).Trim();
             if (rawName.Length == 0)
             {
                 await _db.SaveChangesAsync(cancellationToken);
+                if (purposeChanged)
+                {
+                    // Recompute needs the Purpose change committed first -- a fresh query
+                    // wouldn't see the pending change yet.
+                    await RecomputeAttachmentFlagsAsync(att.JobApplicationId, cancellationToken);
+                    await _db.SaveChangesAsync(cancellationToken);
+                }
                 return NoContent();
             }
 
@@ -130,6 +158,11 @@ namespace JobTrackerApi.Controllers
             att.FileName = name;
             att.FilePath = newPath;
             await _db.SaveChangesAsync(cancellationToken);
+            if (purposeChanged)
+            {
+                await RecomputeAttachmentFlagsAsync(att.JobApplicationId, cancellationToken);
+                await _db.SaveChangesAsync(cancellationToken);
+            }
 
             return NoContent();
         }
@@ -141,8 +174,11 @@ namespace JobTrackerApi.Controllers
             if (att is null) return NotFound();
 
             var path = att.FilePath;
+            var jobId = att.JobApplicationId;
             _db.Attachments.Remove(att);
             await _db.SaveChangesAsync(cancellationToken);
+            await RecomputeAttachmentFlagsAsync(jobId, cancellationToken);
+            await _db.SaveChangesAsync(cancellationToken);
 
             try
             {
@@ -200,6 +236,8 @@ namespace JobTrackerApi.Controllers
                 });
             }
 
+            await _db.SaveChangesAsync(cancellationToken);
+            await RecomputeAttachmentFlagsAsync(jobId, cancellationToken);
             await _db.SaveChangesAsync(cancellationToken);
             return Ok();
         }

JobTrackerApi/Controllers/GmailController.cs

@@ -13,7 +13,7 @@ namespace JobTrackerApi.Controllers;
 [ApiController]
 [Route("api/gmail")]
 [Authorize]
-public sealed class GmailController : ControllerBase
+public sealed partial class GmailController : ControllerBase
 {
     private readonly IGmailOAuthService _gmail;
     private readonly IGmailJobMatchingService _matching;
@@ -37,77 +37,6 @@ public sealed class GmailController : ControllerBase
     private IEmailProvider Email => _providers.Get("gmail")
         ?? throw new InvalidOperationException("Gmail email provider is not registered.");
 
-    public sealed record GmailImportResultDto(int Imported, int Skipped, string? ThreadId);
-    public sealed record GmailImportMessageResultDto(int Imported, int Skipped, string MessageId, string? ThreadId, Correspondence? Message);
-    public sealed record ImportGmailMessageRequest(int JobApplicationId, string MessageId);
-    public sealed record ImportGmailThreadRequest(int JobApplicationId, string ThreadId, string[] MessageIds);
-    public sealed record RefreshLinkedThreadsRequest(int JobApplicationId);
-    public sealed record GmailThreadRefreshThreadDto(string ThreadId, int Imported, int Skipped, int TotalMessages, string Status, DateTimeOffset? LatestMessageDate);
-    public sealed record GmailThreadRefreshResultDto(int JobApplicationId, int ThreadsChecked, int Imported, int Skipped, bool HasLinkedThreads, DateTimeOffset RefreshedAt, IReadOnlyList<GmailThreadRefreshThreadDto> Threads);
-    public sealed record GmailJobMatchReasonDto(string Label, string Value, int Points);
-    public sealed record GmailJobMatchedMessageDto(
-        string Id,
-        string ThreadId,
-        string Subject,
-        string From,
-        string To,
-        DateTimeOffset? Date,
-        string Snippet,
-        int Score,
-        string Confidence,
-        bool AlreadyImported,
-        IReadOnlyList<string> MatchedQueries,
-        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons);
-    public sealed record GmailJobMatchedThreadDto(
-        string ThreadId,
-        string Subject,
-        int Score,
-        string Confidence,
-        bool HasImportedMessages,
-        int ImportedMessageCount,
-        int MessageCount,
-        DateTimeOffset? LatestDate,
-        IReadOnlyList<string> MatchedQueries,
-        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons,
-        IReadOnlyList<GmailJobMatchedMessageDto> Messages);
-    public sealed record GmailJobMatchesResponseDto(
-        int JobApplicationId,
-        string JobTitle,
-        string CompanyName,
-        string? RecruiterName,
-        string? RecruiterEmail,
-        IReadOnlyList<string> Queries,
-        int CandidateMessageCount,
-        int CandidateThreadCount,
-        IReadOnlyList<GmailJobMatchedThreadDto> Threads);
-
-    public sealed record GmailReviewJobCandidateDto(int JobApplicationId, string JobTitle, string CompanyName, int Score, string Confidence, IReadOnlyList<GmailJobMatchReasonDto> Reasons);
-    public sealed record GmailReviewThreadDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, int MessageCount, string Routing, bool HasImportedMessages, string? DecisionNote, IReadOnlyList<string> MatchedQueries, IReadOnlyList<GmailReviewJobCandidateDto> JobCandidates, IReadOnlyList<GmailJobMatchedMessageDto> Messages);
-    public sealed record GmailReviewQueueResponseDto(IReadOnlyList<string> Queries, int CandidateThreadCount, int AutoLinkThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, IReadOnlyList<GmailReviewThreadDto> Threads);
-    public sealed record SaveGmailReviewDecisionRequest(string ThreadId, string Decision, int? JobApplicationId, string? Note);
-    public sealed record GmailManualSyncRequest(int? LookbackDays, int? MaxResultsPerQuery, bool? AutoImportHighConfidence, bool? IncludeSpamTrash);
-    public sealed record GmailManualSyncResultDto(int QueriesRun, int CandidateThreadCount, int AutoLinkedThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, int ImportedMessages, int ImportedThreads, int SkippedMessages, int LookbackDays, bool IncludeSpamTrash, DateTimeOffset SyncedAt);
-    public sealed record GmailSuggestedJobCandidateDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, string? CompanyName, string? RecruiterName, string? RecruiterEmail, string? SuggestedJobTitle, string Routing, IReadOnlyList<string> MatchedQueries, string Preview);
-    public sealed record GmailSuggestedJobsResponseDto(int Count, IReadOnlyList<GmailSuggestedJobCandidateDto> Items);
-    public sealed record CreateSuggestedGmailJobRequest(string ThreadId, string CompanyName, string JobTitle, string? RecruiterName, string? RecruiterEmail, string? Notes, string? Status);
-    public sealed record CreatedSuggestedGmailJobDto(int JobApplicationId, int CompanyId, string ThreadId, int Imported, int Skipped);
-    public sealed record RelinkGmailThreadRequest(int JobApplicationId, string ThreadId, bool RemoveFromOtherJobs, string? Note);
-    public sealed record GmailRelinkResultDto(string ThreadId, int JobApplicationId, int Imported, int Skipped, int UnlinkedMessages);
-    public sealed record UnlinkGmailThreadRequest(int JobApplicationId, string ThreadId, string? Note, string? NextDecision);
-    public sealed record GmailUnlinkResultDto(string ThreadId, int JobApplicationId, int RemovedMessages, string Decision);
-
-    public sealed record GmailConnectionStatusDto(
-        bool Connected,
-        string? GmailAddress,
-        DateTimeOffset? ConnectedAt,
-        DateTimeOffset? LastSyncedAt,
-        DateTimeOffset? LastSyncAttemptedAt,
-        DateTimeOffset? LastSyncSucceededAt,
-        string? LastSyncMode,
-        string? LastSyncSource,
-        string? LastSyncStatus,
-        string? LastSyncError);
-
     [HttpGet("status")]
     public async Task<ActionResult<GmailConnectionStatusDto>> Status(CancellationToken cancellationToken)
     {
@@ -671,7 +600,9 @@ public sealed class GmailController : ControllerBase
             imported++;
         }
 
-        UpsertReviewDecision(await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken), ownerUserId, request.ThreadId.Trim(), "linked", job.Id, request.Notes);
+        var suggestedJobReviewDecision = await _db.GmailReviewDecisions
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == request.ThreadId.Trim(), cancellationToken);
+        UpsertReviewDecision(suggestedJobReviewDecision, ownerUserId, request.ThreadId.Trim(), "linked", job.Id, request.Notes);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new CreatedSuggestedGmailJobDto(job.Id, company.Id, request.ThreadId.Trim(), imported, skipped));
     }
@@ -725,8 +656,9 @@ public sealed class GmailController : ControllerBase
             imported++;
         }
 
-        var reviewDecisions = await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken);
+        var reviewDecision = await _db.GmailReviewDecisions
-        UpsertReviewDecision(reviewDecisions, ownerUserId, threadId, "linked", job.Id, request.Note);
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == threadId, cancellationToken);
+        UpsertReviewDecision(reviewDecision, ownerUserId, threadId, "linked", job.Id, request.Note);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new GmailRelinkResultDto(threadId, job.Id, imported, skipped, unlinkedMessages));
     }
@@ -752,10 +684,11 @@ public sealed class GmailController : ControllerBase
             _db.Correspondences.RemoveRange(messages);
         }
 
-        var reviewDecisions = await _db.GmailReviewDecisions.Where(x => x.OwnerUserId == ownerUserId).ToListAsync(cancellationToken);
+        var reviewDecision = await _db.GmailReviewDecisions
+            .FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId && x.ThreadId == threadId, cancellationToken);
         var nextDecision = (request.NextDecision ?? "review").Trim().ToLowerInvariant();
         if (nextDecision is not ("review" or "suggested" or "rejected")) nextDecision = "review";
-        UpsertReviewDecision(reviewDecisions, ownerUserId, threadId, nextDecision, null, request.Note);
+        UpsertReviewDecision(reviewDecision, ownerUserId, threadId, nextDecision, null, request.Note);
         await _db.SaveChangesAsync(cancellationToken);
         return Ok(new GmailUnlinkResultDto(threadId, job.Id, messages.Count, nextDecision));
     }
@@ -1012,40 +945,6 @@ public sealed class GmailController : ControllerBase
         return _matching.BuildJobQueries(job, queryOverride);
     }
 
-    private static string ApplySyncBoundary(string query, int lookbackDays, bool includeSpamTrash)
-    {
-        var bounded = (query ?? string.Empty).Trim();
-        if (!bounded.Contains("newer_than:", StringComparison.OrdinalIgnoreCase))
-        {
-            bounded = string.IsNullOrWhiteSpace(bounded)
-                ? $"newer_than:{lookbackDays}d"
-                : $"{bounded} newer_than:{lookbackDays}d";
-        }
-
-        if (!includeSpamTrash)
-        {
-            if (!bounded.Contains("in:spam", StringComparison.OrdinalIgnoreCase)) bounded += " -in:spam";
-            if (!bounded.Contains("in:trash", StringComparison.OrdinalIgnoreCase)) bounded += " -in:trash";
-        }
-
-        return bounded.Trim();
-    }
-
-    private static bool LooksLikeJobRelatedThread(IReadOnlyList<GmailQueryMatchedMessage> orderedMessages)
-    {
-        var sample = string.Join("\n", orderedMessages.Select(item => string.Join(" ", new[] { item.Message.Subject, item.Message.From, item.Message.Snippet }.Where(value => !string.IsNullOrWhiteSpace(value)))));
-        if (string.IsNullOrWhiteSpace(sample)) return false;
-        return sample.Contains("interview", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("application", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("recruit", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("role", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("position", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("offer", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("follow up", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("follow-up", StringComparison.OrdinalIgnoreCase)
-            || sample.Contains("rejection", StringComparison.OrdinalIgnoreCase);
-    }
-
     private void UpsertReviewDecision(IDictionary<string, GmailReviewDecision> decisions, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
     {
         if (!decisions.TryGetValue(threadId, out var existing))
@@ -1065,9 +964,11 @@ public sealed class GmailController : ControllerBase
         existing.UpdatedAt = DateTimeOffset.UtcNow;
     }
 
-    private void UpsertReviewDecision(List<GmailReviewDecision> decisions, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
+    // Single-thread upsert: callers acting on exactly one ThreadId should load just that row
+    // (see the FirstOrDefaultAsync call sites below) rather than every review decision for the
+    // owner just to scan for one match.
+    private void UpsertReviewDecision(GmailReviewDecision? existing, string ownerUserId, string threadId, string decision, int? jobApplicationId, string? note)
     {
-        var existing = decisions.FirstOrDefault(x => x.ThreadId == threadId);
         if (existing is null)
         {
             existing = new GmailReviewDecision
@@ -1075,7 +976,6 @@ public sealed class GmailController : ControllerBase
                 OwnerUserId = ownerUserId,
                 ThreadId = threadId,
             };
-            decisions.Add(existing);
             _db.GmailReviewDecisions.Add(existing);
         }
 
@@ -1085,54 +985,6 @@ public sealed class GmailController : ControllerBase
         existing.UpdatedAt = DateTimeOffset.UtcNow;
     }
 
-    private static string ToConfidence(int score)
-    {
-        return score switch
-        {
-            >= 30 => "high",
-            >= 16 => "medium",
-            _ => "low"
-        };
-    }
-
-    private static string? ExtractFirstEmail(string? value)
-    {
-        if (string.IsNullOrWhiteSpace(value)) return null;
-        var match = System.Text.RegularExpressions.Regex.Match(value, @"[A-Z0-9._%+-]+@[A-Z0-9.-]+\.[A-Z]{2,}", System.Text.RegularExpressions.RegexOptions.IgnoreCase);
-        return match.Success ? match.Value : null;
-    }
-
-    private static string? ExtractRecruiterName(string? value)
-    {
-        if (string.IsNullOrWhiteSpace(value)) return null;
-        var trimmed = value.Split('<')[0].Trim().Trim('"');
-        return string.IsNullOrWhiteSpace(trimmed) || trimmed.Contains('@') ? null : trimmed;
-    }
-
-    private static string? ExtractCompanyName(string? from, string? subject)
-    {
-        var subjectText = (subject ?? string.Empty).Trim();
-        if (!string.IsNullOrWhiteSpace(subjectText))
-        {
-            var parts = subjectText.Split(new[] { '-', '–', '|' }, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
-            if (parts.Length >= 2) return parts[0];
-        }
-
-        var recruiterName = ExtractRecruiterName(from);
-        return recruiterName is { Length: > 0 } && recruiterName.Contains(' ') ? recruiterName.Split(' ').Last() : null;
-    }
-
-    private static string? ExtractRoleFromSubject(string? subject)
-    {
-        if (string.IsNullOrWhiteSpace(subject)) return null;
-        var trimmed = subject.Trim();
-        if (trimmed.Contains("interview", StringComparison.OrdinalIgnoreCase))
-        {
-            return trimmed.Replace("interview", string.Empty, StringComparison.OrdinalIgnoreCase).Trim(' ', '-', ':');
-        }
-        return trimmed.Length <= 120 ? trimmed : trimmed[..120];
-    }
-
     private string GetRequiredOwnerUserId()
     {
         return User.FindFirstValue(ClaimTypes.NameIdentifier) ?? User.FindFirstValue("sub")
@@ -1167,29 +1019,4 @@ public sealed class GmailController : ControllerBase
         return $"{Request.Scheme}://{Request.Host}/api/gmail/oauth/callback";
     }
 
-    private static string BuildPopupHtml(bool success, string message)
-    {
-        var escaped = System.Net.WebUtility.HtmlEncode(message);
-        var status = success ? "connected" : "error";
-        var title = success ? "Gmail connected" : "Gmail connection failed";
-        var serializedMessage = System.Text.Json.JsonSerializer.Serialize(message);
-        return $@"<!doctype html>
-<html>
-<head>
-  <meta charset=""utf-8"" />
-  <title>Gmail connection</title>
-</head>
-<body style=""font-family:Segoe UI,Arial,sans-serif;padding:24px;line-height:1.5;"">
-  <h2>{title}</h2>
-  <p>{escaped}</p>
-  <p>You can close this window.</p>
-  <script>
-    if (window.opener) {{
-      window.opener.postMessage({{ source: 'jobtracker-gmail-oauth', status: '{status}', message: {serializedMessage} }}, '*');
-    }}
-    window.close();
-  </script>
-</body>
-</html>";
-    }
 }

JobTrackerApi/Controllers/GmailDtos.cs

@@ -0,0 +1,79 @@
+using JobTrackerApi.Models;
+
+namespace JobTrackerApi.Controllers;
+
+// DTOs for GmailController, split out for readability (Wave 2 safe refactor -- no behaviour
+// change; these were previously nested inline in the controller file).
+public partial class GmailController
+{
+    public sealed record GmailImportResultDto(int Imported, int Skipped, string? ThreadId);
+    public sealed record GmailImportMessageResultDto(int Imported, int Skipped, string MessageId, string? ThreadId, Correspondence? Message);
+    public sealed record ImportGmailMessageRequest(int JobApplicationId, string MessageId);
+    public sealed record ImportGmailThreadRequest(int JobApplicationId, string ThreadId, string[] MessageIds);
+    public sealed record RefreshLinkedThreadsRequest(int JobApplicationId);
+    public sealed record GmailThreadRefreshThreadDto(string ThreadId, int Imported, int Skipped, int TotalMessages, string Status, DateTimeOffset? LatestMessageDate);
+    public sealed record GmailThreadRefreshResultDto(int JobApplicationId, int ThreadsChecked, int Imported, int Skipped, bool HasLinkedThreads, DateTimeOffset RefreshedAt, IReadOnlyList<GmailThreadRefreshThreadDto> Threads);
+    public sealed record GmailJobMatchReasonDto(string Label, string Value, int Points);
+    public sealed record GmailJobMatchedMessageDto(
+        string Id,
+        string ThreadId,
+        string Subject,
+        string From,
+        string To,
+        DateTimeOffset? Date,
+        string Snippet,
+        int Score,
+        string Confidence,
+        bool AlreadyImported,
+        IReadOnlyList<string> MatchedQueries,
+        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons);
+    public sealed record GmailJobMatchedThreadDto(
+        string ThreadId,
+        string Subject,
+        int Score,
+        string Confidence,
+        bool HasImportedMessages,
+        int ImportedMessageCount,
+        int MessageCount,
+        DateTimeOffset? LatestDate,
+        IReadOnlyList<string> MatchedQueries,
+        IReadOnlyList<GmailJobMatchReasonDto> MatchReasons,
+        IReadOnlyList<GmailJobMatchedMessageDto> Messages);
+    public sealed record GmailJobMatchesResponseDto(
+        int JobApplicationId,
+        string JobTitle,
+        string CompanyName,
+        string? RecruiterName,
+        string? RecruiterEmail,
+        IReadOnlyList<string> Queries,
+        int CandidateMessageCount,
+        int CandidateThreadCount,
+        IReadOnlyList<GmailJobMatchedThreadDto> Threads);
+
+    public sealed record GmailReviewJobCandidateDto(int JobApplicationId, string JobTitle, string CompanyName, int Score, string Confidence, IReadOnlyList<GmailJobMatchReasonDto> Reasons);
+    public sealed record GmailReviewThreadDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, int MessageCount, string Routing, bool HasImportedMessages, string? DecisionNote, IReadOnlyList<string> MatchedQueries, IReadOnlyList<GmailReviewJobCandidateDto> JobCandidates, IReadOnlyList<GmailJobMatchedMessageDto> Messages);
+    public sealed record GmailReviewQueueResponseDto(IReadOnlyList<string> Queries, int CandidateThreadCount, int AutoLinkThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, IReadOnlyList<GmailReviewThreadDto> Threads);
+    public sealed record SaveGmailReviewDecisionRequest(string ThreadId, string Decision, int? JobApplicationId, string? Note);
+    public sealed record GmailManualSyncRequest(int? LookbackDays, int? MaxResultsPerQuery, bool? AutoImportHighConfidence, bool? IncludeSpamTrash);
+    public sealed record GmailManualSyncResultDto(int QueriesRun, int CandidateThreadCount, int AutoLinkedThreadCount, int ReviewThreadCount, int UnmatchedThreadCount, int ImportedMessages, int ImportedThreads, int SkippedMessages, int LookbackDays, bool IncludeSpamTrash, DateTimeOffset SyncedAt);
+    public sealed record GmailSuggestedJobCandidateDto(string ThreadId, string Subject, DateTimeOffset? LatestDate, string? CompanyName, string? RecruiterName, string? RecruiterEmail, string? SuggestedJobTitle, string Routing, IReadOnlyList<string> MatchedQueries, string Preview);
+    public sealed record GmailSuggestedJobsResponseDto(int Count, IReadOnlyList<GmailSuggestedJobCandidateDto> Items);
+    public sealed record CreateSuggestedGmailJobRequest(string ThreadId, string CompanyName, string JobTitle, string? RecruiterName, string? RecruiterEmail, string? Notes, string? Status);
+    public sealed record CreatedSuggestedGmailJobDto(int JobApplicationId, int CompanyId, string ThreadId, int Imported, int Skipped);
+    public sealed record RelinkGmailThreadRequest(int JobApplicationId, string ThreadId, bool RemoveFromOtherJobs, string? Note);
+    public sealed record GmailRelinkResultDto(string ThreadId, int JobApplicationId, int Imported, int Skipped, int UnlinkedMessages);
+    public sealed record UnlinkGmailThreadRequest(int JobApplicationId, string ThreadId, string? Note, string? NextDecision);
+    public sealed record GmailUnlinkResultDto(string ThreadId, int JobApplicationId, int RemovedMessages, string Decision);
+
+    public sealed record GmailConnectionStatusDto(
+        bool Connected,
+        string? GmailAddress,
+        DateTimeOffset? ConnectedAt,
+        DateTimeOffset? LastSyncedAt,
+        DateTimeOffset? LastSyncAttemptedAt,
+        DateTimeOffset? LastSyncSucceededAt,
+        string? LastSyncMode,
+        string? LastSyncSource,
+        string? LastSyncStatus,
+        string? LastSyncError);
+}

JobTrackerApi/Controllers/GmailParsing.cs

@@ -0,0 +1,116 @@
+using JobTrackerApi.Services;
+
+namespace JobTrackerApi.Controllers;
+
+// Pure parsing/formatting helpers for GmailController, split out for readability (Wave 2 safe
+// refactor -- no behaviour change). All are static and side-effect free.
+public sealed partial class GmailController
+{
+    private static string ApplySyncBoundary(string query, int lookbackDays, bool includeSpamTrash)
+    {
+        var bounded = (query ?? string.Empty).Trim();
+        if (!bounded.Contains("newer_than:", StringComparison.OrdinalIgnoreCase))
+        {
+            bounded = string.IsNullOrWhiteSpace(bounded)
+                ? $"newer_than:{lookbackDays}d"
+                : $"{bounded} newer_than:{lookbackDays}d";
+        }
+
+        if (!includeSpamTrash)
+        {
+            if (!bounded.Contains("in:spam", StringComparison.OrdinalIgnoreCase)) bounded += " -in:spam";
+            if (!bounded.Contains("in:trash", StringComparison.OrdinalIgnoreCase)) bounded += " -in:trash";
+        }
+
+        return bounded.Trim();
+    }
+
+    private static bool LooksLikeJobRelatedThread(IReadOnlyList<GmailQueryMatchedMessage> orderedMessages)
+    {
+        var sample = string.Join("\n", orderedMessages.Select(item => string.Join(" ", new[] { item.Message.Subject, item.Message.From, item.Message.Snippet }.Where(value => !string.IsNullOrWhiteSpace(value)))));
+        if (string.IsNullOrWhiteSpace(sample)) return false;
+        return sample.Contains("interview", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("application", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("recruit", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("role", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("position", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("offer", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("follow up", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("follow-up", StringComparison.OrdinalIgnoreCase)
+            || sample.Contains("rejection", StringComparison.OrdinalIgnoreCase);
+    }
+
+    private static string ToConfidence(int score)
+    {
+        return score switch
+        {
+            >= 30 => "high",
+            >= 16 => "medium",
+            _ => "low"
+        };
+    }
+
+    private static string? ExtractFirstEmail(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+        var match = System.Text.RegularExpressions.Regex.Match(value, @"[A-Z0-9._%+-]+@[A-Z0-9.-]+\.[A-Z]{2,}", System.Text.RegularExpressions.RegexOptions.IgnoreCase);
+        return match.Success ? match.Value : null;
+    }
+
+    private static string? ExtractRecruiterName(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+        var trimmed = value.Split('<')[0].Trim().Trim('"');
+        return string.IsNullOrWhiteSpace(trimmed) || trimmed.Contains('@') ? null : trimmed;
+    }
+
+    private static string? ExtractCompanyName(string? from, string? subject)
+    {
+        var subjectText = (subject ?? string.Empty).Trim();
+        if (!string.IsNullOrWhiteSpace(subjectText))
+        {
+            var parts = subjectText.Split(new[] { '-', '–', '|' }, StringSplitOptions.RemoveEmptyEntries | StringSplitOptions.TrimEntries);
+            if (parts.Length >= 2) return parts[0];
+        }
+
+        var recruiterName = ExtractRecruiterName(from);
+        return recruiterName is { Length: > 0 } && recruiterName.Contains(' ') ? recruiterName.Split(' ').Last() : null;
+    }
+
+    private static string? ExtractRoleFromSubject(string? subject)
+    {
+        if (string.IsNullOrWhiteSpace(subject)) return null;
+        var trimmed = subject.Trim();
+        if (trimmed.Contains("interview", StringComparison.OrdinalIgnoreCase))
+        {
+            return trimmed.Replace("interview", string.Empty, StringComparison.OrdinalIgnoreCase).Trim(' ', '-', ':');
+        }
+        return trimmed.Length <= 120 ? trimmed : trimmed[..120];
+    }
+
+    private static string BuildPopupHtml(bool success, string message)
+    {
+        var escaped = System.Net.WebUtility.HtmlEncode(message);
+        var status = success ? "connected" : "error";
+        var title = success ? "Gmail connected" : "Gmail connection failed";
+        var serializedMessage = System.Text.Json.JsonSerializer.Serialize(message);
+        return $@"<!doctype html>
+<html>
+<head>
+  <meta charset=""utf-8"" />
+  <title>Gmail connection</title>
+</head>
+<body style=""font-family:Segoe UI,Arial,sans-serif;padding:24px;line-height:1.5;"">
+  <h2>{title}</h2>
+  <p>{escaped}</p>
+  <p>You can close this window.</p>
+  <script>
+    if (window.opener) {{
+      window.opener.postMessage({{ source: 'jobtracker-gmail-oauth', status: '{status}', message: {serializedMessage} }}, '*');
+    }}
+    window.close();
+  </script>
+</body>
+</html>";
+    }
+}

JobTrackerApi/Controllers/JobApplicationsController.cs

@@ -1376,11 +1376,7 @@ Canonical profile:
             string? CoverLetterText,
             string? JobUrl,
             DateTime? DateApplied,
-            DateTime? FeedbackRequestedAt,
+            DateTime? FeedbackRequestedAt
-            bool? HasResume,
-            bool? HasCoverLetter,
-            bool? HasPortfolio,
-            bool? HasOtherAttachment
         );
 
         private static (decimal? Min, decimal? Max, string? Currency, string? Period) NormalizeSalary(
@@ -1422,10 +1418,9 @@ Canonical profile:
                 NextAction = string.IsNullOrWhiteSpace(request.NextAction) ? null : request.NextAction.Trim(),
                 FollowUpAt = request.FollowUpAt,
                 FeedbackRequestedAt = request.FeedbackRequestedAt,
-                HasResume = request.HasResume ?? false,
+                // HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
-                HasCoverLetter = request.HasCoverLetter ?? false,
+                // Attachment rows (see AttachmentsController.RecomputeAttachmentFlagsAsync), not
-                HasPortfolio = request.HasPortfolio ?? false,
+                // settable here -- they start false and get set correctly once files are uploaded.
-                HasOtherAttachment = request.HasOtherAttachment ?? false,
                 Notes = string.IsNullOrWhiteSpace(request.Notes) ? null : request.Notes,
                 Description = string.IsNullOrWhiteSpace(request.Description) ? null : request.Description,
                 TranslatedDescription = string.IsNullOrWhiteSpace(request.TranslatedDescription) ? null : request.TranslatedDescription,
@@ -1486,10 +1481,6 @@ Canonical profile:
             string? SalaryPeriod,
             string? NextAction,
             DateTime? FollowUpAt,
-            bool? HasResume,
-            bool? HasCoverLetter,
-            bool? HasPortfolio,
-            bool? HasOtherAttachment,
             string? Notes,
             string? Description,
             string? TranslatedDescription,
@@ -1529,10 +1520,8 @@ Canonical profile:
             job.NextAction = string.IsNullOrWhiteSpace(request.NextAction) ? null : request.NextAction.Trim();
             job.FollowUpAt = request.FollowUpAt;
             job.FeedbackRequestedAt = request.FeedbackRequestedAt;
-            if (request.HasResume is not null) job.HasResume = request.HasResume.Value;
+            // HasResume/HasCoverLetter/HasPortfolio/HasOtherAttachment are derived from
-            if (request.HasCoverLetter is not null) job.HasCoverLetter = request.HasCoverLetter.Value;
+            // Attachment rows, not settable here -- see AttachmentsController.RecomputeAttachmentFlagsAsync.
-            if (request.HasPortfolio is not null) job.HasPortfolio = request.HasPortfolio.Value;
-            if (request.HasOtherAttachment is not null) job.HasOtherAttachment = request.HasOtherAttachment.Value;
             job.Notes = request.Notes;
             job.Description = request.Description;
             job.TranslatedDescription = request.TranslatedDescription;

Models/JobApplication.cs

@@ -24,7 +24,9 @@ public class JobApplication
     public DateTime? FeedbackRequestedAt { get; set; }
     public string? RecruiterMessageDraft { get; set; }
 
-    // Attachment checklist
+    // Attachment checklist. Derived from Attachment rows, not directly settable by API
+    // consumers -- see AttachmentsController.RecomputeAttachmentFlagsAsync, the single place
+    // these are written, so they can't drift from what's actually attached.
     public bool HasResume { get; set; } = false;
     public bool HasCoverLetter { get; set; } = false;
     public bool HasPortfolio { get; set; } = false;

job-tracker-ui/src/components/AddJobModal.tsx

@@ -327,10 +327,6 @@ export default function AddJobModal({ open, onClose, onCreated, initialUrl }: Pr
         notes,
         coverLetterText: null,
         dateApplied,
-        hasResume: attachments.resume.length > 0,
-        hasCoverLetter: attachments.coverLetter.length > 0,
-        hasPortfolio: attachments.portfolio.length > 0,
-        hasOtherAttachment: attachments.other.length > 0,
       });
 
       if (response.data?.id && attachmentCount > 0) {

job-tracker-ui/src/components/EditJobDialog.tsx

@@ -158,10 +158,6 @@ export default function EditJobDialog({ open, jobId, onClose, onSaved }: Props)
         salaryPeriod: salaryPeriod || null,
         nextAction: nextAction.trim() || null,
         followUpAt: followUpAt || null,
-        hasResume,
-        hasCoverLetter,
-        hasPortfolio,
-        hasOtherAttachment,
         notes: notes || null,
         description: description || null,
         translatedDescription: translatedDescription || null,
@@ -243,16 +239,13 @@ export default function EditJobDialog({ open, jobId, onClose, onSaved }: Props)
 
           <Paper variant="outlined" sx={{ p: 2 }}>
             <Typography variant="overline" sx={{ color: "text.secondary" }}>{t("editJobAttachmentsChecklist")}</Typography>
-            <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap", mt: 1, mb: 1.5 }}>
+            {/* Derived from actual uploaded attachments (see the Attachments panel) -- not
+                manually editable, so this can never drift from what's really attached. */}
+            <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap", mt: 1 }}>
               <Chip size="small" label={hasResume ? t("editJobResumeReady") : t("editJobResumeMissing")} color={hasResume ? "success" : "default"} variant={hasResume ? "filled" : "outlined"} />
               <Chip size="small" label={hasCoverLetter ? t("editJobCoverLetterReady") : t("editJobCoverLetterMissing")} color={hasCoverLetter ? "success" : "default"} variant={hasCoverLetter ? "filled" : "outlined"} />
               <Chip size="small" label={hasPortfolio ? t("editJobPortfolioReady") : t("editJobPortfolioOptional")} color={hasPortfolio ? "success" : "default"} variant={hasPortfolio ? "filled" : "outlined"} />
-            </Box>
+              {hasOtherAttachment && <Chip size="small" label={t("editJobOtherAttachment")} color="success" variant="filled" />}
-            <Box sx={{ display: "flex", gap: 2, flexWrap: "wrap", mt: 1 }}>
-              <FormControlLabel control={<Checkbox checked={hasResume} onChange={(e) => setHasResume(e.target.checked)} />} label={t("editJobResume")} />
-              <FormControlLabel control={<Checkbox checked={hasCoverLetter} onChange={(e) => setHasCoverLetter(e.target.checked)} />} label={t("editJobCoverLetter")} />
-              <FormControlLabel control={<Checkbox checked={hasPortfolio} onChange={(e) => setHasPortfolio(e.target.checked)} />} label={t("editJobPortfolio")} />
-              <FormControlLabel control={<Checkbox checked={hasOtherAttachment} onChange={(e) => setHasOtherAttachment(e.target.checked)} />} label={t("editJobOtherAttachment")} />
             </Box>
           </Paper>
         </Box>