feat: enrich gmail correspondence metadata

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

@@ -258,7 +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");
 
@@ -272,6 +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);
@@ -315,7 +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",
@@ -326,7 +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" });
@@ -398,7 +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;
@@ -414,12 +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

@@ -753,6 +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.
@@ -780,6 +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;");
 
@@ -879,6 +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;");

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
 {
@@ -321,9 +322,13 @@ public sealed class GmailOAuthService : IGmailOAuthService
 
             var threadId = root.TryGetProperty("threadId", out var threadEl) ? threadEl.GetString() ?? "" : "";
             var snippet = root.TryGetProperty("snippet", out var snippetEl) ? snippetEl.GetString() ?? "" : "";
+            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))
@@ -345,7 +350,9 @@ public sealed class GmailOAuthService : IGmailOAuthService
                 headers.TryGetValue("date", out var dateRaw) && DateTimeOffset.TryParse(dateRaw, out var parsedDate) ? parsedDate : null,
                 snippet,
                 bodyText.Trim(),
-                string.IsNullOrWhiteSpace(bodyHtml) ? null : bodyHtml
+                string.IsNullOrWhiteSpace(bodyHtml) ? null : bodyHtml,
+                labels,
+                attachments
             );
         }
         catch (Exception ex)
@@ -538,6 +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; }
     }
 }

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 }}>

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 {