Merge feature branch feat/gmail-job-correspondence

Data/JobTrackerContext.cs

@@ -66,6 +66,8 @@ namespace JobTrackerApi.Data
         modelBuilder.Entity<GmailConnection>()
             .HasQueryFilter(x => CurrentUserId == null || x.OwnerUserId == CurrentUserId);
 
+        modelBuilder.Ignore<CorrespondenceAttachmentMetadata>();
+
         modelBuilder.Entity<GmailConnection>()
             .HasIndex(x => new { x.OwnerUserId, x.GmailAddress })
             .IsUnique();

JobTrackerApi.Tests/GmailControllerTests.cs

@@ -15,6 +15,39 @@ namespace JobTrackerApi.Tests;
 
 public sealed class GmailControllerTests
 {
+    [Fact]
+    public async Task Status_returns_sync_state_fields_for_connected_account()
+    {
+        await using var db = CreateDb();
+        var gmail = new Mock<IGmailOAuthService>();
+        gmail.Setup(service => service.GetConnectionAsync("user-1", It.IsAny<CancellationToken>()))
+            .ReturnsAsync(new GmailConnection
+            {
+                OwnerUserId = "user-1",
+                GmailAddress = "user@example.test",
+                ConnectedAt = DateTimeOffset.UtcNow.AddDays(-3),
+                LastSyncedAt = DateTimeOffset.UtcNow.AddMinutes(-10),
+                LastSyncAttemptedAt = DateTimeOffset.UtcNow.AddMinutes(-5),
+                LastSyncSucceededAt = DateTimeOffset.UtcNow.AddMinutes(-10),
+                LastSyncMode = "list-messages",
+                LastSyncSource = "custom-query",
+                LastSyncStatus = "error",
+                LastSyncError = "Token refresh failed"
+            });
+
+        var controller = CreateController(db, gmail.Object, "user-1");
+        var result = await controller.Status(CancellationToken.None);
+
+        var ok = Assert.IsType<OkObjectResult>(result.Result);
+        var payload = Assert.IsType<GmailController.GmailConnectionStatusDto>(ok.Value);
+        Assert.True(payload.Connected);
+        Assert.Equal("user@example.test", payload.GmailAddress);
+        Assert.Equal("list-messages", payload.LastSyncMode);
+        Assert.Equal("custom-query", payload.LastSyncSource);
+        Assert.Equal("error", payload.LastSyncStatus);
+        Assert.Equal("Token refresh failed", payload.LastSyncError);
+    }
+
     [Fact]
     public async Task Import_thread_rejects_missing_message_ids()
     {
@@ -225,7 +258,9 @@ public sealed class GmailControllerTests
                 DateTimeOffset.UtcNow.AddDays(-1),
                 "Snippet",
                 "Body text",
-                null));
+                null,
+                new[] { "INBOX", "IMPORTANT" },
+                new[] { new GmailMessageAttachment("cv.pdf", "application/pdf", 2048, "att-1", false) }));
 
         var controller = CreateController(db, gmail.Object, "user-1");
 
@@ -239,6 +274,10 @@ public sealed class GmailControllerTests
         Assert.Equal("thread-1", firstPayload.Message!.ExternalThreadId);
         Assert.Equal("Maria Recruiter <maria@acme.test>", firstPayload.Message.ExternalFrom);
         Assert.Equal("user@example.test", firstPayload.Message.ExternalTo);
+        Assert.Equal("inbound", firstPayload.Message.Direction);
+        Assert.Contains("IMPORTANT", firstPayload.Message.ExternalLabels);
+        Assert.Single(firstPayload.Message.AttachmentMetadata);
+        Assert.Equal("cv.pdf", firstPayload.Message.AttachmentMetadata[0].FileName);
 
         var second = await controller.Import(new GmailController.ImportGmailMessageRequest(job.Id, "msg-1"), CancellationToken.None);
         var secondOk = Assert.IsType<OkObjectResult>(second.Result);
@@ -282,7 +321,9 @@ public sealed class GmailControllerTests
                 DateTimeOffset.UtcNow.AddDays(-1),
                 "Snippet 1",
                 "Body text 1",
-                null));
+                null,
+                Array.Empty<string>(),
+                Array.Empty<GmailMessageAttachment>()));
         gmail.Setup(service => service.GetMessageAsync("user-1", "msg-2", It.IsAny<CancellationToken>()))
             .ReturnsAsync(new GmailMessageDetail(
                 "msg-2",
@@ -293,7 +334,9 @@ public sealed class GmailControllerTests
                 DateTimeOffset.UtcNow,
                 "Snippet 2",
                 "Body text 2",
-                null));
+                null,
+                Array.Empty<string>(),
+                Array.Empty<GmailMessageAttachment>()));
 
         var controller = CreateController(db, gmail.Object, "user-1");
         var request = new GmailController.ImportGmailThreadRequest(job.Id, "thread-1", new[] { "msg-1", "msg-2" });
@@ -365,7 +408,9 @@ public sealed class GmailControllerTests
                 DateTimeOffset.UtcNow,
                 "New reply",
                 "Reply body",
-                null));
+                null,
+                Array.Empty<string>(),
+                Array.Empty<GmailMessageAttachment>()));
 
         var controller = CreateController(db, gmail.Object, "user-1");
         var result = await controller.RefreshLinkedThreads(new GmailController.RefreshLinkedThreadsRequest(job.Id), CancellationToken.None);

JobTrackerApi/Controllers/CorrespondenceController.cs

@@ -48,10 +48,13 @@ namespace JobTrackerApi.Controllers
             string? Subject,
             string? Channel,
             DateTime? Date,
+            string? Direction,
             string? ExternalMessageId,
             string? ExternalThreadId,
             string? ExternalFrom,
-            string? ExternalTo
+            string? ExternalTo,
+            string? ExternalLabelsJson,
+            string? AttachmentMetadataJson
         );
 
         // POST new message
@@ -71,10 +74,13 @@ namespace JobTrackerApi.Controllers
                 From = request.From.Trim(),
                 Subject = string.IsNullOrWhiteSpace(request.Subject) ? null : request.Subject.Trim(),
                 Channel = string.IsNullOrWhiteSpace(request.Channel) ? null : request.Channel.Trim(),
+                Direction = string.IsNullOrWhiteSpace(request.Direction) ? null : request.Direction.Trim(),
                 ExternalMessageId = string.IsNullOrWhiteSpace(request.ExternalMessageId) ? null : request.ExternalMessageId.Trim(),
                 ExternalThreadId = string.IsNullOrWhiteSpace(request.ExternalThreadId) ? null : request.ExternalThreadId.Trim(),
                 ExternalFrom = string.IsNullOrWhiteSpace(request.ExternalFrom) ? null : request.ExternalFrom.Trim(),
                 ExternalTo = string.IsNullOrWhiteSpace(request.ExternalTo) ? null : request.ExternalTo.Trim(),
+                ExternalLabelsJson = string.IsNullOrWhiteSpace(request.ExternalLabelsJson) ? null : request.ExternalLabelsJson.Trim(),
+                AttachmentMetadataJson = string.IsNullOrWhiteSpace(request.AttachmentMetadataJson) ? null : request.AttachmentMetadataJson.Trim(),
                 Content = request.Content,
                 Date = request.Date ?? DateTime.Now,
             };

JobTrackerApi/Controllers/GmailController.cs

@@ -1,4 +1,5 @@
 using System.Security.Claims;
+using System.Text.Json;
 using JobTrackerApi.Data;
 using JobTrackerApi.Models;
 using JobTrackerApi.Services;
@@ -68,18 +69,34 @@ public sealed class GmailController : ControllerBase
         int CandidateThreadCount,
         IReadOnlyList<GmailJobMatchedThreadDto> Threads);
 
+    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<IActionResult> Status(CancellationToken cancellationToken)
+    public async Task<ActionResult<GmailConnectionStatusDto>> Status(CancellationToken cancellationToken)
     {
         var ownerUserId = GetRequiredOwnerUserId();
         var connection = await _gmail.GetConnectionAsync(ownerUserId, cancellationToken);
-        return Ok(new
+        return Ok(new GmailConnectionStatusDto(
-        {
+            connection is not null,
-            connected = connection is not null,
+            connection?.GmailAddress,
-            gmailAddress = connection?.GmailAddress,
+            connection?.ConnectedAt,
-            connectedAt = connection?.ConnectedAt,
+            connection?.LastSyncedAt,
-            lastSyncedAt = connection?.LastSyncedAt,
+            connection?.LastSyncAttemptedAt,
-        });
+            connection?.LastSyncSucceededAt,
+            connection?.LastSyncMode,
+            connection?.LastSyncSource,
+            connection?.LastSyncStatus,
+            connection?.LastSyncError));
     }
 
     [HttpGet("connect-url")]
@@ -398,12 +415,22 @@ public sealed class GmailController : ControllerBase
         {
             JobApplicationId = job.Id,
             From = isMe ? "Me" : "Company",
+            Direction = isMe ? "outbound" : "inbound",
             Subject = string.IsNullOrWhiteSpace(detail.Subject) ? null : detail.Subject.Trim(),
             Channel = "Email",
             ExternalMessageId = detail.Id,
             ExternalThreadId = string.IsNullOrWhiteSpace(detail.ThreadId) ? null : detail.ThreadId.Trim(),
             ExternalFrom = string.IsNullOrWhiteSpace(detail.From) ? null : detail.From.Trim(),
             ExternalTo = string.IsNullOrWhiteSpace(detail.To) ? null : detail.To.Trim(),
+            ExternalLabelsJson = detail.Labels.Count == 0 ? null : JsonSerializer.Serialize(detail.Labels),
+            AttachmentMetadataJson = detail.Attachments.Count == 0 ? null : JsonSerializer.Serialize(detail.Attachments.Select(attachment => new CorrespondenceAttachmentMetadata
+            {
+                FileName = attachment.FileName,
+                MimeType = attachment.MimeType,
+                SizeBytes = attachment.SizeBytes,
+                GmailAttachmentId = attachment.GmailAttachmentId,
+                Inline = attachment.Inline,
+            })),
             Content = string.IsNullOrWhiteSpace(detail.BodyText) ? detail.Snippet : detail.BodyText,
             Date = messageDate,
         };

JobTrackerApi/Program.cs

@@ -135,6 +135,7 @@ builder.Services.AddSingleton<ISummarizerService, SummarizerService>();
 builder.Services.AddSingleton<ICvAiClassifier, CvAiClassifier>();
 builder.Services.AddSingleton<IGoogleTokenValidator, GoogleTokenValidator>();
 builder.Services.AddScoped<IGmailOAuthService, GmailOAuthService>();
+builder.Services.AddSingleton<IGmailCorrespondenceEnrichmentService, NoOpGmailCorrespondenceEnrichmentService>();
 
 builder.Services.AddIdentityCore<ApplicationUser>(options =>
     {
@@ -628,10 +629,23 @@ CREATE TABLE IF NOT EXISTS "GmailConnections" (
     "AccessTokenExpiresAt" TEXT NULL,
     "Scope" TEXT NOT NULL,
     "ConnectedAt" TEXT NOT NULL,
-    "LastSyncedAt" TEXT NULL
+    "LastSyncedAt" TEXT NULL,
+    "LastSyncAttemptedAt" TEXT NULL,
+    "LastSyncSucceededAt" TEXT NULL,
+    "LastSyncMode" TEXT NULL,
+    "LastSyncSource" TEXT NULL,
+    "LastSyncStatus" TEXT NULL,
+    "LastSyncError" TEXT NULL
 );
 """);
 
+            EnsureColumn(c, "GmailConnections", "LastSyncAttemptedAt", "ALTER TABLE GmailConnections ADD COLUMN LastSyncAttemptedAt TEXT NULL;");
+            EnsureColumn(c, "GmailConnections", "LastSyncSucceededAt", "ALTER TABLE GmailConnections ADD COLUMN LastSyncSucceededAt TEXT NULL;");
+            EnsureColumn(c, "GmailConnections", "LastSyncMode", "ALTER TABLE GmailConnections ADD COLUMN LastSyncMode TEXT NULL;");
+            EnsureColumn(c, "GmailConnections", "LastSyncSource", "ALTER TABLE GmailConnections ADD COLUMN LastSyncSource TEXT NULL;");
+            EnsureColumn(c, "GmailConnections", "LastSyncStatus", "ALTER TABLE GmailConnections ADD COLUMN LastSyncStatus TEXT NULL;");
+            EnsureColumn(c, "GmailConnections", "LastSyncError", "ALTER TABLE GmailConnections ADD COLUMN LastSyncError TEXT NULL;");
+
             Exec(c, """CREATE INDEX IF NOT EXISTS "IX_GmailConnections_OwnerUserId" ON "GmailConnections" ("OwnerUserId");""");
             Exec(c, """CREATE UNIQUE INDEX IF NOT EXISTS "IX_GmailConnections_OwnerUserId_GmailAddress" ON "GmailConnections" ("OwnerUserId", "GmailAddress");""");
         }
@@ -739,6 +753,9 @@ CREATE TABLE IF NOT EXISTS "TailoredCvDrafts" (
                 EnsureColumn(conn, "Correspondences", "ExternalThreadId", "ALTER TABLE Correspondences ADD COLUMN ExternalThreadId TEXT NULL;");
                 EnsureColumn(conn, "Correspondences", "ExternalFrom", "ALTER TABLE Correspondences ADD COLUMN ExternalFrom TEXT NULL;");
                 EnsureColumn(conn, "Correspondences", "ExternalTo", "ALTER TABLE Correspondences ADD COLUMN ExternalTo TEXT NULL;");
+                EnsureColumn(conn, "Correspondences", "Direction", "ALTER TABLE Correspondences ADD COLUMN Direction TEXT NULL;");
+                EnsureColumn(conn, "Correspondences", "ExternalLabelsJson", "ALTER TABLE Correspondences ADD COLUMN ExternalLabelsJson TEXT NULL;");
+                EnsureColumn(conn, "Correspondences", "AttachmentMetadataJson", "ALTER TABLE Correspondences ADD COLUMN AttachmentMetadataJson TEXT NULL;");
             }
 
             // Record the migration as applied.
@@ -766,6 +783,9 @@ CREATE TABLE IF NOT EXISTS "TailoredCvDrafts" (
         EnsureColumn(conn, "Correspondences", "ExternalThreadId", "ALTER TABLE Correspondences ADD COLUMN ExternalThreadId TEXT NULL;");
         EnsureColumn(conn, "Correspondences", "ExternalFrom", "ALTER TABLE Correspondences ADD COLUMN ExternalFrom TEXT NULL;");
         EnsureColumn(conn, "Correspondences", "ExternalTo", "ALTER TABLE Correspondences ADD COLUMN ExternalTo TEXT NULL;");
+        EnsureColumn(conn, "Correspondences", "Direction", "ALTER TABLE Correspondences ADD COLUMN Direction TEXT NULL;");
+        EnsureColumn(conn, "Correspondences", "ExternalLabelsJson", "ALTER TABLE Correspondences ADD COLUMN ExternalLabelsJson TEXT NULL;");
+        EnsureColumn(conn, "Correspondences", "AttachmentMetadataJson", "ALTER TABLE Correspondences ADD COLUMN AttachmentMetadataJson TEXT NULL;");
         EnsureColumn(conn, "Attachments", "Purpose", "ALTER TABLE Attachments ADD COLUMN Purpose TEXT NULL;");
         EnsureColumn(conn, "Attachments", "UseForAi", "ALTER TABLE Attachments ADD COLUMN UseForAi INTEGER NOT NULL DEFAULT 1;");
 
@@ -865,6 +885,9 @@ CREATE TABLE IF NOT EXISTS "TailoredCvDrafts" (
             EnsureMySqlColumn(conn, "Correspondences", "ExternalThreadId", "ALTER TABLE `Correspondences` ADD COLUMN `ExternalThreadId` longtext NULL;");
             EnsureMySqlColumn(conn, "Correspondences", "ExternalFrom", "ALTER TABLE `Correspondences` ADD COLUMN `ExternalFrom` longtext NULL;");
             EnsureMySqlColumn(conn, "Correspondences", "ExternalTo", "ALTER TABLE `Correspondences` ADD COLUMN `ExternalTo` longtext NULL;");
+            EnsureMySqlColumn(conn, "Correspondences", "Direction", "ALTER TABLE `Correspondences` ADD COLUMN `Direction` varchar(100) NULL;");
+            EnsureMySqlColumn(conn, "Correspondences", "ExternalLabelsJson", "ALTER TABLE `Correspondences` ADD COLUMN `ExternalLabelsJson` longtext NULL;");
+            EnsureMySqlColumn(conn, "Correspondences", "AttachmentMetadataJson", "ALTER TABLE `Correspondences` ADD COLUMN `AttachmentMetadataJson` longtext NULL;");
             EnsureMySqlColumn(conn, "Attachments", "Purpose", "ALTER TABLE `Attachments` ADD COLUMN `Purpose` varchar(100) NULL;");
             EnsureMySqlColumn(conn, "Attachments", "UseForAi", "ALTER TABLE `Attachments` ADD COLUMN `UseForAi` tinyint(1) NOT NULL DEFAULT 1;");
             EnsureMySqlColumn(conn, "AspNetUsers", "ProfileCvText", "ALTER TABLE `AspNetUsers` ADD COLUMN `ProfileCvText` longtext NULL;");
@@ -939,6 +962,37 @@ CONSTRAINT `FK_CvExtractionRuns_CvUploadArtifacts_ArtifactId` FOREIGN KEY (`Arti
                 cmd.ExecuteNonQuery();
             }
 
+            if (!HasMySqlTable(conn, "GmailConnections"))
+            {
+                using var cmd = conn.CreateCommand();
+                cmd.CommandText = @"CREATE TABLE IF NOT EXISTS `GmailConnections` (
+`Id` int NOT NULL AUTO_INCREMENT,
+`OwnerUserId` varchar(255) NOT NULL,
+`GmailAddress` varchar(512) NOT NULL,
+`EncryptedRefreshToken` longtext NOT NULL,
+`EncryptedAccessToken` longtext NULL,
+`AccessTokenExpiresAt` datetime(6) NULL,
+`Scope` longtext NOT NULL,
+`ConnectedAt` datetime(6) NOT NULL,
+`LastSyncedAt` datetime(6) NULL,
+`LastSyncAttemptedAt` datetime(6) NULL,
+`LastSyncSucceededAt` datetime(6) NULL,
+`LastSyncMode` varchar(255) NULL,
+`LastSyncSource` varchar(255) NULL,
+`LastSyncStatus` varchar(255) NULL,
+`LastSyncError` longtext NULL,
+PRIMARY KEY (`Id`)
+);";
+                cmd.ExecuteNonQuery();
+            }
+
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncAttemptedAt", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncAttemptedAt` datetime(6) NULL;");
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncSucceededAt", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncSucceededAt` datetime(6) NULL;");
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncMode", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncMode` varchar(255) NULL;");
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncSource", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncSource` varchar(255) NULL;");
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncStatus", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncStatus` varchar(255) NULL;");
+            EnsureMySqlColumn(conn, "GmailConnections", "LastSyncError", "ALTER TABLE `GmailConnections` ADD COLUMN `LastSyncError` longtext NULL;");
+
             if (!HasMySqlTable(conn, "TailoredCvDrafts"))
             {
                 using var cmd = conn.CreateCommand();
@@ -1000,6 +1054,20 @@ CONSTRAINT `FK_TailoredCvDrafts_JobApplications_JobApplicationId` FOREIGN KEY (`
                 cmd.ExecuteNonQuery();
             }
 
+            if (!MySqlIndexExists(conn, "GmailConnections", "IX_GmailConnections_OwnerUserId"))
+            {
+                using var cmd = conn.CreateCommand();
+                cmd.CommandText = "CREATE INDEX `IX_GmailConnections_OwnerUserId` ON `GmailConnections` (`OwnerUserId`);";
+                cmd.ExecuteNonQuery();
+            }
+
+            if (!MySqlIndexExists(conn, "GmailConnections", "IX_GmailConnections_OwnerUserId_GmailAddress"))
+            {
+                using var cmd = conn.CreateCommand();
+                cmd.CommandText = "CREATE UNIQUE INDEX `IX_GmailConnections_OwnerUserId_GmailAddress` ON `GmailConnections` (`OwnerUserId`, `GmailAddress`);";
+                cmd.ExecuteNonQuery();
+            }
+
             if (!MySqlIndexExists(conn, "TailoredCvDrafts", "IX_TailoredCvDrafts_OwnerUserId_JobApplicationId"))
             {
                 using var cmd = conn.CreateCommand();

JobTrackerApi/Services/GmailCorrespondenceEnrichment.cs

@@ -0,0 +1,21 @@
+namespace JobTrackerApi.Services;
+
+public sealed record GmailSemanticMatchCandidate(
+    int? JobApplicationId,
+    string? Confidence,
+    string? Reason,
+    IReadOnlyList<string>? ExtractedCompanies,
+    IReadOnlyList<string>? ExtractedRecruiters,
+    IReadOnlyList<string>? ExtractedRoles,
+    IReadOnlyList<string>? ExtractedHints);
+
+public interface IGmailCorrespondenceEnrichmentService
+{
+    Task<GmailSemanticMatchCandidate?> EnrichAsync(string threadSubject, string from, string to, string snippet, string? bodyText, CancellationToken cancellationToken = default);
+}
+
+public sealed class NoOpGmailCorrespondenceEnrichmentService : IGmailCorrespondenceEnrichmentService
+{
+    public Task<GmailSemanticMatchCandidate?> EnrichAsync(string threadSubject, string from, string to, string snippet, string? bodyText, CancellationToken cancellationToken = default)
+        => Task.FromResult<GmailSemanticMatchCandidate?>(null);
+}

JobTrackerApi/Services/GmailOAuthService.cs

@@ -27,7 +27,8 @@ public interface IGmailOAuthService
 public sealed record GmailOAuthExchangeResult(string GmailAddress);
 public sealed record GmailMessageSummary(string Id, string ThreadId, string Subject, string From, string To, DateTimeOffset? Date, string Snippet);
 public sealed record GmailQueryMatchedMessage(GmailMessageSummary Message, IReadOnlyList<string> MatchedQueries);
-public sealed record GmailMessageDetail(string Id, string ThreadId, string Subject, string From, string To, DateTimeOffset? Date, string Snippet, string BodyText, string? BodyHtml);
+public sealed record GmailMessageAttachment(string? FileName, string? MimeType, long? SizeBytes, string? GmailAttachmentId, bool Inline);
+public sealed record GmailMessageDetail(string Id, string ThreadId, string Subject, string From, string To, DateTimeOffset? Date, string Snippet, string BodyText, string? BodyHtml, IReadOnlyList<string> Labels, IReadOnlyList<GmailMessageAttachment> Attachments);
 
 internal sealed class GmailTokenResponse
 {
@@ -116,6 +117,12 @@ public sealed class GmailOAuthService : IGmailOAuthService
         existing.AccessTokenExpiresAt = DateTimeOffset.UtcNow.AddSeconds(Math.Max(tokens.expires_in - 60, 60));
         existing.Scope = tokens.scope?.Trim() ?? Scope;
         existing.ConnectedAt = DateTimeOffset.UtcNow;
+        existing.LastSyncStatus = "connected";
+        existing.LastSyncSource = "oauth-callback";
+        existing.LastSyncMode = "connect";
+        existing.LastSyncError = null;
+        existing.LastSyncAttemptedAt = DateTimeOffset.UtcNow;
+        existing.LastSyncSucceededAt = existing.LastSyncAttemptedAt;
 
         await _db.SaveChangesAsync(cancellationToken);
         return new GmailOAuthExchangeResult(existing.GmailAddress);
@@ -148,40 +155,49 @@ public sealed class GmailOAuthService : IGmailOAuthService
     public async Task<IReadOnlyList<GmailMessageSummary>> ListMessagesAsync(string ownerUserId, string? query, int maxResults, CancellationToken cancellationToken)
     {
         maxResults = Math.Clamp(maxResults, 1, 25);
-        var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
+        try
-        var client = _httpClientFactory.CreateClient();
-        client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
-
-        var url = $"https://gmail.googleapis.com/gmail/v1/users/me/messages?maxResults={maxResults}";
-        if (!string.IsNullOrWhiteSpace(query))
         {
-            url += $"&q={Uri.EscapeDataString(query.Trim())}";
+            var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
+            var client = _httpClientFactory.CreateClient();
+            client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
+
+            var url = $"https://gmail.googleapis.com/gmail/v1/users/me/messages?maxResults={maxResults}";
+            if (!string.IsNullOrWhiteSpace(query))
+            {
+                url += $"&q={Uri.EscapeDataString(query.Trim())}";
+            }
+
+            using var response = await client.GetAsync(url, cancellationToken);
+            response.EnsureSuccessStatusCode();
+
+            using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
+            if (!doc.RootElement.TryGetProperty("messages", out var messagesElement) || messagesElement.ValueKind != JsonValueKind.Array)
+            {
+                await TouchSyncStateAsync(ownerUserId, "list-messages", string.IsNullOrWhiteSpace(query) ? "default-query" : "custom-query", true, null, cancellationToken);
+                return Array.Empty<GmailMessageSummary>();
+            }
+
+            var ids = messagesElement.EnumerateArray()
+                .Select(x => x.TryGetProperty("id", out var id) ? id.GetString() : null)
+                .Where(x => !string.IsNullOrWhiteSpace(x))
+                .Cast<string>()
+                .ToList();
+
+            var results = new List<GmailMessageSummary>(ids.Count);
+            foreach (var id in ids)
+            {
+                var detail = await GetMessageAsync(ownerUserId, id, cancellationToken);
+                results.Add(new GmailMessageSummary(detail.Id, detail.ThreadId, detail.Subject, detail.From, detail.To, detail.Date, detail.Snippet));
+            }
+
+            await TouchSyncStateAsync(ownerUserId, "list-messages", string.IsNullOrWhiteSpace(query) ? "default-query" : "custom-query", true, null, cancellationToken);
+            return results;
         }
-
+        catch (Exception ex)
-        using var response = await client.GetAsync(url, cancellationToken);
-        response.EnsureSuccessStatusCode();
-
-        using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
-        if (!doc.RootElement.TryGetProperty("messages", out var messagesElement) || messagesElement.ValueKind != JsonValueKind.Array)
         {
-            return Array.Empty<GmailMessageSummary>();
+            await TouchSyncStateAsync(ownerUserId, "list-messages", string.IsNullOrWhiteSpace(query) ? "default-query" : "custom-query", false, ex.Message, cancellationToken);
+            throw;
         }
-
-        var ids = messagesElement.EnumerateArray()
-            .Select(x => x.TryGetProperty("id", out var id) ? id.GetString() : null)
-            .Where(x => !string.IsNullOrWhiteSpace(x))
-            .Cast<string>()
-            .ToList();
-
-        var results = new List<GmailMessageSummary>(ids.Count);
-        foreach (var id in ids)
-        {
-            var detail = await GetMessageAsync(ownerUserId, id, cancellationToken);
-            results.Add(new GmailMessageSummary(detail.Id, detail.ThreadId, detail.Subject, detail.From, detail.To, detail.Date, detail.Snippet));
-        }
-
-        await TouchSyncTimeAsync(ownerUserId, cancellationToken);
-        return results;
     }
 
     public async Task<IReadOnlyList<GmailMessageSummary>> ListMessagesForQueriesAsync(string ownerUserId, IEnumerable<string> queries, int maxResultsPerQuery, CancellationToken cancellationToken)
@@ -233,93 +249,117 @@ public sealed class GmailOAuthService : IGmailOAuthService
             return Array.Empty<GmailMessageSummary>();
         }
 
-        var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
+        try
-        var client = _httpClientFactory.CreateClient();
-        client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
-
-        var url = $"https://gmail.googleapis.com/gmail/v1/users/me/threads/{Uri.EscapeDataString(threadId.Trim())}?format=metadata&metadataHeaders=Subject&metadataHeaders=From&metadataHeaders=To&metadataHeaders=Date";
-        using var response = await client.GetAsync(url, cancellationToken);
-        response.EnsureSuccessStatusCode();
-
-        using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
-        if (!doc.RootElement.TryGetProperty("messages", out var messagesElement) || messagesElement.ValueKind != JsonValueKind.Array)
         {
-            return Array.Empty<GmailMessageSummary>();
+            var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
-        }
+            var client = _httpClientFactory.CreateClient();
+            client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
 
-        var results = new List<GmailMessageSummary>();
+            var url = $"https://gmail.googleapis.com/gmail/v1/users/me/threads/{Uri.EscapeDataString(threadId.Trim())}?format=metadata&metadataHeaders=Subject&metadataHeaders=From&metadataHeaders=To&metadataHeaders=Date";
-        foreach (var messageElement in messagesElement.EnumerateArray())
+            using var response = await client.GetAsync(url, cancellationToken);
-        {
+            response.EnsureSuccessStatusCode();
-            var id = messageElement.TryGetProperty("id", out var idEl) ? idEl.GetString() : null;
-            if (string.IsNullOrWhiteSpace(id)) continue;
 
-            var messageThreadId = messageElement.TryGetProperty("threadId", out var messageThreadIdEl)
+            using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
-                ? messageThreadIdEl.GetString() ?? threadId.Trim()
+            if (!doc.RootElement.TryGetProperty("messages", out var messagesElement) || messagesElement.ValueKind != JsonValueKind.Array)
-                : threadId.Trim();
-            var snippet = messageElement.TryGetProperty("snippet", out var snippetEl) ? snippetEl.GetString() ?? string.Empty : string.Empty;
-            var payload = messageElement.TryGetProperty("payload", out var payloadEl) ? payloadEl : default;
-            var headers = payload.ValueKind == JsonValueKind.Object ? ReadHeaders(payload) : new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
-
-            DateTimeOffset? date = null;
-            if (headers.TryGetValue("date", out var dateHeader) && DateTimeOffset.TryParse(dateHeader, out var parsedDate))
             {
-                date = parsedDate;
+                await TouchSyncStateAsync(ownerUserId, "thread-refresh", "thread-metadata", true, null, cancellationToken);
+                return Array.Empty<GmailMessageSummary>();
             }
 
-            results.Add(new GmailMessageSummary(
+            var results = new List<GmailMessageSummary>();
-                id.Trim(),
+            foreach (var messageElement in messagesElement.EnumerateArray())
-                messageThreadId,
+            {
-                headers.TryGetValue("subject", out var subject) ? subject : string.Empty,
+                var id = messageElement.TryGetProperty("id", out var idEl) ? idEl.GetString() : null;
-                headers.TryGetValue("from", out var from) ? from : string.Empty,
+                if (string.IsNullOrWhiteSpace(id)) continue;
-                headers.TryGetValue("to", out var to) ? to : string.Empty,
-                date,
-                snippet));
-        }
 
-        await TouchSyncTimeAsync(ownerUserId, cancellationToken);
+                var messageThreadId = messageElement.TryGetProperty("threadId", out var messageThreadIdEl)
-        return results;
+                    ? messageThreadIdEl.GetString() ?? threadId.Trim()
+                    : threadId.Trim();
+                var snippet = messageElement.TryGetProperty("snippet", out var snippetEl) ? snippetEl.GetString() ?? string.Empty : string.Empty;
+                var payload = messageElement.TryGetProperty("payload", out var payloadEl) ? payloadEl : default;
+                var headers = payload.ValueKind == JsonValueKind.Object ? ReadHeaders(payload) : new Dictionary<string, string>(StringComparer.OrdinalIgnoreCase);
+
+                DateTimeOffset? date = null;
+                if (headers.TryGetValue("date", out var dateHeader) && DateTimeOffset.TryParse(dateHeader, out var parsedDate))
+                {
+                    date = parsedDate;
+                }
+
+                results.Add(new GmailMessageSummary(
+                    id.Trim(),
+                    messageThreadId,
+                    headers.TryGetValue("subject", out var subject) ? subject : string.Empty,
+                    headers.TryGetValue("from", out var from) ? from : string.Empty,
+                    headers.TryGetValue("to", out var to) ? to : string.Empty,
+                    date,
+                    snippet));
+            }
+
+            await TouchSyncStateAsync(ownerUserId, "thread-refresh", "thread-metadata", true, null, cancellationToken);
+            return results;
+        }
+        catch (Exception ex)
+        {
+            await TouchSyncStateAsync(ownerUserId, "thread-refresh", "thread-metadata", false, ex.Message, cancellationToken);
+            throw;
+        }
     }
 
     public async Task<GmailMessageDetail> GetMessageAsync(string ownerUserId, string messageId, CancellationToken cancellationToken)
     {
-        var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
+        try
-        var client = _httpClientFactory.CreateClient();
-        client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
-
-        var url = $"https://gmail.googleapis.com/gmail/v1/users/me/messages/{Uri.EscapeDataString(messageId)}?format=full";
-        using var response = await client.GetAsync(url, cancellationToken);
-        response.EnsureSuccessStatusCode();
-
-        using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
-        var root = doc.RootElement;
-
-        var threadId = root.TryGetProperty("threadId", out var threadEl) ? threadEl.GetString() ?? "" : "";
-        var snippet = root.TryGetProperty("snippet", out var snippetEl) ? snippetEl.GetString() ?? "" : "";
-
-        var payload = root.GetProperty("payload");
-        var headers = ReadHeaders(payload);
-        var bodyText = ExtractBody(payload, "text/plain");
-        var bodyHtml = ExtractBody(payload, "text/html");
-        if (string.IsNullOrWhiteSpace(bodyText) && !string.IsNullOrWhiteSpace(bodyHtml))
         {
-            bodyText = StripHtml(bodyHtml);
+            var accessToken = await GetValidAccessTokenAsync(ownerUserId, cancellationToken);
-        }
+            var client = _httpClientFactory.CreateClient();
-        else if (LooksLikeHtml(bodyText))
+            client.DefaultRequestHeaders.Authorization = new AuthenticationHeaderValue("Bearer", accessToken);
-        {
-            bodyText = StripHtml(bodyText);
-        }
 
-        return new GmailMessageDetail(
+            var url = $"https://gmail.googleapis.com/gmail/v1/users/me/messages/{Uri.EscapeDataString(messageId)}?format=full";
-            messageId,
+            using var response = await client.GetAsync(url, cancellationToken);
-            threadId,
+            response.EnsureSuccessStatusCode();
-            headers.TryGetValue("subject", out var subject) ? subject : "",
+
-            headers.TryGetValue("from", out var from) ? from : "",
+            using var doc = await JsonDocument.ParseAsync(await response.Content.ReadAsStreamAsync(cancellationToken), cancellationToken: cancellationToken);
-            headers.TryGetValue("to", out var to) ? to : "",
+            var root = doc.RootElement;
-            headers.TryGetValue("date", out var dateRaw) && DateTimeOffset.TryParse(dateRaw, out var parsedDate) ? parsedDate : null,
+
-            snippet,
+            var threadId = root.TryGetProperty("threadId", out var threadEl) ? threadEl.GetString() ?? "" : "";
-            bodyText.Trim(),
+            var snippet = root.TryGetProperty("snippet", out var snippetEl) ? snippetEl.GetString() ?? "" : "";
-            string.IsNullOrWhiteSpace(bodyHtml) ? null : bodyHtml
+            var labels = root.TryGetProperty("labelIds", out var labelIdsEl) && labelIdsEl.ValueKind == JsonValueKind.Array
-        );
+                ? labelIdsEl.EnumerateArray().Where(x => x.ValueKind == JsonValueKind.String).Select(x => x.GetString()).Where(x => !string.IsNullOrWhiteSpace(x)).Cast<string>().ToList()
+                : new List<string>();
+
+            var payload = root.GetProperty("payload");
+            var headers = ReadHeaders(payload);
+            var attachments = ReadAttachments(payload);
+            var bodyText = ExtractBody(payload, "text/plain");
+            var bodyHtml = ExtractBody(payload, "text/html");
+            if (string.IsNullOrWhiteSpace(bodyText) && !string.IsNullOrWhiteSpace(bodyHtml))
+            {
+                bodyText = StripHtml(bodyHtml);
+            }
+            else if (LooksLikeHtml(bodyText))
+            {
+                bodyText = StripHtml(bodyText);
+            }
+
+            await TouchSyncStateAsync(ownerUserId, "message-detail", "gmail-message", true, null, cancellationToken);
+            return new GmailMessageDetail(
+                messageId,
+                threadId,
+                headers.TryGetValue("subject", out var subject) ? subject : "",
+                headers.TryGetValue("from", out var from) ? from : "",
+                headers.TryGetValue("to", out var to) ? to : "",
+                headers.TryGetValue("date", out var dateRaw) && DateTimeOffset.TryParse(dateRaw, out var parsedDate) ? parsedDate : null,
+                snippet,
+                bodyText.Trim(),
+                string.IsNullOrWhiteSpace(bodyHtml) ? null : bodyHtml,
+                labels,
+                attachments
+            );
+        }
+        catch (Exception ex)
+        {
+            await TouchSyncStateAsync(ownerUserId, "message-detail", "gmail-message", false, ex.Message, cancellationToken);
+            throw;
+        }
     }
 
     private async Task<string> GetValidAccessTokenAsync(string ownerUserId, CancellationToken cancellationToken)
@@ -435,13 +475,37 @@ public sealed class GmailOAuthService : IGmailOAuthService
     }
 
     private async Task TouchSyncTimeAsync(string ownerUserId, CancellationToken cancellationToken)
+    {
+        await TouchSyncStateAsync(ownerUserId, "sync", "gmail", true, null, cancellationToken);
+    }
+
+    private async Task TouchSyncStateAsync(string ownerUserId, string mode, string source, bool succeeded, string? error, CancellationToken cancellationToken)
     {
         var connection = await _db.GmailConnections.FirstOrDefaultAsync(x => x.OwnerUserId == ownerUserId, cancellationToken);
         if (connection is null) return;
-        connection.LastSyncedAt = DateTimeOffset.UtcNow;
+
+        var now = DateTimeOffset.UtcNow;
+        connection.LastSyncAttemptedAt = now;
+        connection.LastSyncMode = mode;
+        connection.LastSyncSource = source;
+        connection.LastSyncStatus = succeeded ? "success" : "error";
+        connection.LastSyncError = succeeded ? null : TrimError(error);
+        if (succeeded)
+        {
+            connection.LastSyncedAt = now;
+            connection.LastSyncSucceededAt = now;
+        }
+
         await _db.SaveChangesAsync(cancellationToken);
     }
 
+    private static string? TrimError(string? value)
+    {
+        if (string.IsNullOrWhiteSpace(value)) return null;
+        var trimmed = value.Trim();
+        return trimmed.Length <= 300 ? trimmed : trimmed[..300];
+    }
+
     private string GetRequiredClientId()
     {
         return (_cfg["Google:ClientId"] ?? _cfg["Auth:GoogleClientId"] ?? "").Trim() switch
@@ -481,6 +545,48 @@ public sealed class GmailOAuthService : IGmailOAuthService
         return result;
     }
 
+    private static List<GmailMessageAttachment> ReadAttachments(JsonElement payload)
+    {
+        var results = new List<GmailMessageAttachment>();
+        ReadAttachmentsRecursive(payload, results);
+        return results;
+    }
+
+    private static void ReadAttachmentsRecursive(JsonElement payload, List<GmailMessageAttachment> results)
+    {
+        var body = payload.TryGetProperty("body", out var bodyEl) && bodyEl.ValueKind == JsonValueKind.Object
+            ? bodyEl
+            : default;
+        var gmailAttachmentId = body.ValueKind == JsonValueKind.Object && body.TryGetProperty("attachmentId", out var attachmentIdEl) && attachmentIdEl.ValueKind == JsonValueKind.String
+            ? attachmentIdEl.GetString()
+            : null;
+        var filename = payload.TryGetProperty("filename", out var filenameEl) ? filenameEl.GetString() : null;
+        var mimeType = payload.TryGetProperty("mimeType", out var mimeTypeEl) ? mimeTypeEl.GetString() : null;
+        var sizeBytes = body.ValueKind == JsonValueKind.Object && body.TryGetProperty("size", out var sizeEl) && sizeEl.ValueKind == JsonValueKind.Number
+            ? sizeEl.GetInt64()
+            : (long?)null;
+        var disposition = payload.TryGetProperty("headers", out var headersEl) && headersEl.ValueKind == JsonValueKind.Array
+            ? headersEl.EnumerateArray()
+                .Where(h => h.TryGetProperty("name", out var n) && string.Equals(n.GetString(), "Content-Disposition", StringComparison.OrdinalIgnoreCase))
+                .Select(h => h.TryGetProperty("value", out var v) ? v.GetString() : null)
+                .FirstOrDefault()
+            : null;
+        var isInline = !string.IsNullOrWhiteSpace(disposition) && disposition.Contains("inline", StringComparison.OrdinalIgnoreCase);
+
+        if (!string.IsNullOrWhiteSpace(gmailAttachmentId) || !string.IsNullOrWhiteSpace(filename))
+        {
+            results.Add(new GmailMessageAttachment(filename, mimeType, sizeBytes, gmailAttachmentId, isInline));
+        }
+
+        if (payload.TryGetProperty("parts", out var partsEl) && partsEl.ValueKind == JsonValueKind.Array)
+        {
+            foreach (var part in partsEl.EnumerateArray())
+            {
+                ReadAttachmentsRecursive(part, results);
+            }
+        }
+    }
+
     private static string ExtractBody(JsonElement payload, string mimeType)
     {
         if (payload.TryGetProperty("mimeType", out var mimeTypeEl) &&

Models/Correspondence.cs

@@ -1,4 +1,5 @@
 using System;
+using System.Collections.Generic;
 using System.Text.Json.Serialization;
 
 namespace JobTrackerApi.Models
@@ -11,13 +12,35 @@ namespace JobTrackerApi.Models
         [JsonIgnore]
         public JobApplication JobApplication { get; set; } = null!;
         public string From { get; set; } = ""; // "Me" or "Company"
+        public string? Direction { get; set; } // inbound, outbound, internal, unknown
         public string? Subject { get; set; }
         public string? Channel { get; set; } // e.g. Email, Call, Note
         public string? ExternalMessageId { get; set; }
         public string? ExternalThreadId { get; set; }
         public string? ExternalFrom { get; set; }
         public string? ExternalTo { get; set; }
+        public string? ExternalLabelsJson { get; set; }
+        public string? AttachmentMetadataJson { get; set; }
         public string Content { get; set; } = "";
         public DateTime Date { get; set; } = DateTime.Now;
+
+        [JsonIgnore]
+        public IReadOnlyList<string> ExternalLabels => string.IsNullOrWhiteSpace(ExternalLabelsJson)
+            ? Array.Empty<string>()
+            : (System.Text.Json.JsonSerializer.Deserialize<List<string>>(ExternalLabelsJson) ?? new List<string>());
+
+        [JsonIgnore]
+        public IReadOnlyList<CorrespondenceAttachmentMetadata> AttachmentMetadata => string.IsNullOrWhiteSpace(AttachmentMetadataJson)
+            ? Array.Empty<CorrespondenceAttachmentMetadata>()
+            : (System.Text.Json.JsonSerializer.Deserialize<List<CorrespondenceAttachmentMetadata>>(AttachmentMetadataJson) ?? new List<CorrespondenceAttachmentMetadata>());
+    }
+
+    public sealed class CorrespondenceAttachmentMetadata
+    {
+        public string? FileName { get; set; }
+        public string? MimeType { get; set; }
+        public long? SizeBytes { get; set; }
+        public string? GmailAttachmentId { get; set; }
+        public bool Inline { get; set; }
     }
 }

Models/GmailConnection.cs

@@ -11,4 +11,10 @@ public sealed class GmailConnection
     public string Scope { get; set; } = "";
     public DateTimeOffset ConnectedAt { get; set; } = DateTimeOffset.UtcNow;
     public DateTimeOffset? LastSyncedAt { get; set; }
+    public DateTimeOffset? LastSyncAttemptedAt { get; set; }
+    public DateTimeOffset? LastSyncSucceededAt { get; set; }
+    public string? LastSyncMode { get; set; }
+    public string? LastSyncSource { get; set; }
+    public string? LastSyncStatus { get; set; }
+    public string? LastSyncError { get; set; }
 }

SMART_GMAIL_PROGRESS.md

@@ -0,0 +1,44 @@
+# Smart Gmail Job Correspondence Integration Progress
+
+## Branch
+- feat/gmail-job-correspondence
+
+## Status
+- Workstream initialized.
+- Milestones planned: M006-M010.
+- Current focus: M006 / S01 foundation work.
+
+## Completed so far
+- Created separate Gmail feature branch.
+- Captured foundation context in `.gsd/milestones/M006/M006-CONTEXT.md`.
+- Planned milestones M006-M010 for the Gmail workstream.
+- Planned slice M006/S01.
+- Confirmed existing architecture seams:
+  - Gmail OAuth/token flow already exists.
+  - Per-job Gmail candidate search/import/thread refresh already exists.
+  - Correspondence persistence already stores Gmail thread/message metadata.
+  - Current implementation is job-local, not global-inbox/review oriented.
+- Implemented M006/S01 foundation changes:
+  - durable Gmail sync-state fields on `GmailConnection`
+  - SQLite/MySQL bootstrap support for new Gmail sync-state columns
+  - richer `GET /api/gmail/status` response
+  - per-job correspondence UI now shows sync diagnostics
+  - focused backend/frontend Gmail tests added and passing
+  - Phase 2 extension seam scaffolded with a no-op enrichment service
+  - Phase 1/2 design doc added at `docs/gmail-correspondence-phase1.md`
+- Started M007 ingestion/storage work:
+  - imported correspondence now stores direction, Gmail labels JSON, and attachment metadata JSON
+  - Gmail message detail extraction now reads labels and attachment metadata from Gmail payloads
+  - focused Gmail backend/frontend tests pass against the richer import contract
+
+## Next tasks
+1. Implement M006/S01/T01: refactor Gmail connection foundation and sync-state model.
+2. Implement M006/S01/T02: expose sync-state surfaces in UI without breaking current correspondence workflow.
+3. Implement M006/S01/T03: prepare Phase 2 extension seam/docs.
+4. Verify backend + frontend Gmail focused tests.
+5. Commit and push incremental progress.
+
+## Resume notes
+- Previous CV/parsing branch work is separate and already pushed.
+- Local dev SQLite runtime still has missing-table drift in some unrelated surfaces (`RuleSettings`, `Companies`, etc.); avoid conflating that with the Gmail feature work.
+- Existing per-job Gmail tests live in `JobTrackerApi.Tests/GmailControllerTests.cs` and `job-tracker-ui/src/correspondence-gmail-import.test.tsx`.

docs/gmail-correspondence-phase1.md

@@ -0,0 +1,55 @@
+# Smart Gmail Job Correspondence Integration
+
+## Phase split
+
+### Phase 1
+Deterministic, high-trust Gmail job correspondence integration:
+- OAuth/account connection
+- token refresh lifecycle
+- sync-state tracking
+- manual sync/backfill
+- dedup by Gmail message id
+- deterministic job-linking + confidence routing
+- review queue for medium-confidence items
+- unmatched thread suggestions
+- global inbox + per-job timeline
+
+### Phase 2
+Prepared, not deeply implemented in this slice:
+- semantic Gmail-to-job disambiguation
+- richer recruiter/company/role extraction
+- stage/status hinting
+- interview/rejection/offer extraction
+- follow-up/reply suggestion generation
+
+## Foundation decisions
+
+- Phase 1 remains useful without AI/Ollama.
+- Deterministic evidence remains the primary truth source.
+- Future AI enrichment attaches reasons/confidence alongside deterministic evidence rather than replacing it.
+- Gmail sync state is now durable on the Gmail connection record:
+  - `LastSyncAttemptedAt`
+  - `LastSyncSucceededAt`
+  - `LastSyncMode`
+  - `LastSyncSource`
+  - `LastSyncStatus`
+  - `LastSyncError`
+
+## Current code seams
+
+- Gmail OAuth and token lifecycle: `JobTrackerApi/Services/GmailOAuthService.cs`
+- Gmail endpoints: `JobTrackerApi/Controllers/GmailController.cs`
+- Gmail connection persistence: `Models/GmailConnection.cs`
+- Correspondence persistence: `Models/Correspondence.cs`
+- Per-job correspondence UX: `job-tracker-ui/src/components/Correspondence.tsx`
+- Future Phase 2 AI seam: `JobTrackerApi/Services/GmailCorrespondenceEnrichment.cs`
+
+## What Phase 2 should plug into later
+
+The `IGmailCorrespondenceEnrichmentService` seam is intended to accept normalized Gmail message/thread context and return optional semantic hints:
+- probable job match
+- richer confidence rationale
+- extracted recruiter/company/role entities
+- lightweight stage hints
+
+Phase 1 should never require this service to return anything useful. The default runtime implementation remains a no-op.

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

@@ -382,11 +382,13 @@ export default function Correspondence({ jobId, job }: { jobId: number; job: Job
                   <Box sx={{ maxWidth: "80%", borderRadius: 3, p: 1.25, border: `1px solid ${alpha(accent, theme.palette.mode === "dark" ? 0.32 : 0.22)}`, background: alpha(accent, theme.palette.mode === "dark" ? 0.14 : 0.1), color: "text.primary" }}>
                     {m.subject ? <Typography sx={{ fontWeight: 800, mb: 0.5 }}>{m.subject}</Typography> : null}
                     <Typography sx={{ whiteSpace: "pre-wrap", lineHeight: 1.35 }}>{m.content}</Typography>
-                    {(m.externalThreadId || m.externalFrom || m.externalTo) ? (
+                    {(m.externalThreadId || m.externalFrom || m.externalTo || m.externalLabelsJson || m.attachmentMetadataJson) ? (
                       <Box sx={{ display: "flex", gap: 0.75, flexWrap: "wrap", mt: 1 }}>
                         {m.externalThreadId ? <Chip size="small" label={`Thread ${m.externalThreadId}`} variant="outlined" /> : null}
                         {m.externalFrom ? <Chip size="small" label={`From ${m.externalFrom}`} variant="outlined" /> : null}
                         {m.externalTo ? <Chip size="small" label={`To ${m.externalTo}`} variant="outlined" /> : null}
+                        {m.externalLabelsJson ? <Chip size="small" label={`${JSON.parse(m.externalLabelsJson).length} Gmail label${JSON.parse(m.externalLabelsJson).length === 1 ? "" : "s"}`} variant="outlined" /> : null}
+                        {m.attachmentMetadataJson ? <Chip size="small" label={`${JSON.parse(m.attachmentMetadataJson).length} attachment${JSON.parse(m.attachmentMetadataJson).length === 1 ? "" : "s"}`} variant="outlined" /> : null}
                       </Box>
                     ) : null}
                     <Box sx={{ display: "flex", justifyContent: "space-between", gap: 1, alignItems: "flex-end", mt: 0.75 }}>
@@ -413,6 +415,16 @@ export default function Correspondence({ jobId, job }: { jobId: number; job: Job
         <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap" }}>
           <Chip size="small" color={gmailStatus?.connected ? "success" : "default"} variant="outlined" label={gmailStatus?.connected ? "Gmail connected" : "Gmail not connected"} />
           <Chip size="small" color={linkedThreadIds.length > 0 ? "success" : "default"} variant="outlined" label={linkedThreadIds.length > 0 ? `Linked threads: ${linkedThreadIds.length}` : "No linked threads yet"} />
+          {gmailStatus?.lastSyncStatus ? (
+            <Chip
+              size="small"
+              color={gmailStatus.lastSyncStatus === "success" ? "success" : "warning"}
+              variant="outlined"
+              label={gmailStatus.lastSyncStatus === "success"
+                ? `Last Gmail sync ${gmailStatus.lastSyncMode || "sync"} ok`
+                : `Last Gmail sync ${gmailStatus.lastSyncMode || "sync"} failed`}
+            />
+          ) : null}
           {linkedThreadRefresh ? (
             <Chip
               size="small"
@@ -425,6 +437,11 @@ export default function Correspondence({ jobId, job }: { jobId: number; job: Job
             />
           ) : null}
         </Box>
+        {gmailStatus?.lastSyncError ? (
+          <Typography variant="body2" sx={{ color: "warning.main", mt: 1 }}>
+            Latest Gmail sync issue: {gmailStatus.lastSyncError}
+          </Typography>
+        ) : null}
       </Box>
 
       <Box sx={{ display: "flex", gap: 1, alignItems: "flex-start", mt: 1.5, flexWrap: "wrap" }}>
@@ -503,6 +520,8 @@ export default function Correspondence({ jobId, job }: { jobId: number; job: Job
                     </Box>
                   ) : null}
                   {gmailStatus.lastSyncedAt ? <Chip label={t("correspondenceLastSynced", { date: new Date(gmailStatus.lastSyncedAt).toLocaleString() })} size="small" /> : null}
+                  {gmailStatus.lastSyncAttemptedAt ? <Chip label={`Sync checked ${new Date(gmailStatus.lastSyncAttemptedAt).toLocaleString()}`} size="small" variant="outlined" /> : null}
+                  {gmailStatus.lastSyncStatus === "error" && gmailStatus.lastSyncError ? <Chip label={`Sync issue: ${gmailStatus.lastSyncError}`} size="small" color="warning" variant="outlined" /> : null}
                   {linkedThreadIds.length > 0 ? (
                     <Box sx={{ display: "flex", gap: 1, flexWrap: "wrap" }}>
                       <Chip size="small" color="success" variant="outlined" label={`Linked threads: ${linkedThreadIds.length}`} />

job-tracker-ui/src/correspondence-gmail-import.test.tsx

@@ -78,7 +78,7 @@ describe("correspondence Gmail import", () => {
         return Promise.resolve({ data: correspondenceMessages } as any);
       }
       if (url === "/gmail/status") {
-        return Promise.resolve({ data: { connected: true, gmailAddress: "user@example.test", lastSyncedAt: new Date().toISOString() } } as any);
+        return Promise.resolve({ data: { connected: true, gmailAddress: "user@example.test", lastSyncedAt: new Date().toISOString(), lastSyncAttemptedAt: new Date().toISOString(), lastSyncMode: "list-messages", lastSyncSource: "custom-query", lastSyncStatus: "error", lastSyncError: "Token refresh failed" } } as any);
       }
       if (url === "/gmail/job-candidates") {
         return Promise.resolve({
@@ -291,6 +291,16 @@ describe("correspondence Gmail import", () => {
     expect((await screen.findAllByText(/thread thread-1/i)).length).toBeGreaterThan(0);
   });
 
+  test("shows Gmail sync state diagnostics alongside linked thread continuity", async () => {
+    renderDialog();
+
+    fireEvent.click(await screen.findByRole("button", { name: /import email/i }));
+    fireEvent.click(await screen.findByRole("tab", { name: /^google$/i }));
+
+    expect(await screen.findByText(/sync checked/i)).toBeInTheDocument();
+    expect((await screen.findAllByText(/token refresh failed/i)).length).toBeGreaterThan(0);
+  });
+
   test("manual Gmail search override reloads job candidates with queryOverride", async () => {
     renderDialog();
 

job-tracker-ui/src/types.ts

@@ -200,10 +200,19 @@ export interface SaveApplicationDraftsRequest {
   recruiterMessageDraft?: string | null;
 }
 
+export interface CorrespondenceAttachmentMetadata {
+  fileName?: string | null;
+  mimeType?: string | null;
+  sizeBytes?: number | null;
+  gmailAttachmentId?: string | null;
+  inline?: boolean;
+}
+
 export interface CorrespondenceMessage {
   id: number;
   jobApplicationId: number;
   from: string;
+  direction?: string | null;
   content: string;
   subject?: string;
   channel?: string;
@@ -212,6 +221,8 @@ export interface CorrespondenceMessage {
   externalThreadId?: string | null;
   externalFrom?: string | null;
   externalTo?: string | null;
+  externalLabelsJson?: string | null;
+  attachmentMetadataJson?: string | null;
 }
 
 export interface GmailJobMatchReason {
@@ -293,6 +304,12 @@ export interface GmailStatus {
   gmailAddress?: string;
   connectedAt?: string;
   lastSyncedAt?: string;
+  lastSyncAttemptedAt?: string;
+  lastSyncSucceededAt?: string;
+  lastSyncMode?: string | null;
+  lastSyncSource?: string | null;
+  lastSyncStatus?: string | null;
+  lastSyncError?: string | null;
 }
 
 export interface GmailMessageSummary {