From 24ac7ac796e3e73bb04893387163c762dbf67d1f Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Andr=C3=A9=20Padez?= <andre.padez@gmail.com>
Date: Thu, 12 Mar 2026 07:24:44 +0000
Subject: [PATCH] replace gmail resync with Gmail REST API, remove mbsync
 dependency

First sync still uses IMAP with app password. Subsequent syncs use
Gmail API history.list + messages.get with OAuth for faster, more
reliable incremental sync. Dispatch gmail-sync handler for gmail
accounts instead of generic email-sync. Show sync button for synced
accounts.

Co-Authored-By: Claude Opus 4.6 <noreply@anthropic.com>
---
 scripts/reimport-gmail.ts                     |  33 -
 .../IntegrationsSettings/EmailAccounts.tsx    |   4 +-
 src/servers/api/email/accounts.ts             |   6 +-
 src/servers/data-path.ts                      |   1 -
 src/servers/queue/handlers/gmail-sync.ts      | 827 ++++++++----------
 5 files changed, 382 insertions(+), 489 deletions(-)
 delete mode 100644 scripts/reimport-gmail.ts

diff --git a/scripts/reimport-gmail.ts b/scripts/reimport-gmail.ts
deleted file mode 100644
index ade78d0f..00000000
--- a/scripts/reimport-gmail.ts
+++ /dev/null
@@ -1,33 +0,0 @@
-import { join } from 'node:path';
-import { unlinkSync } from 'node:fs';
-import { openEmailDb } from '../src/servers/api/email/email-db';
-import { importMaildir } from '../src/servers/queue/handlers/gmail-sync';
-
-const DATA_PATH = process.env.DATA_PATH ?? join(process.cwd(), 'data');
-const email = process.argv[2];
-
-if (!email) {
-  console.error('Usage: bun scripts/reimport-gmail.ts <email>');
-  process.exit(1);
-}
-
-const maildirPath = join(DATA_PATH, email, 'Gmail', 'Maildir');
-const dbPath = join(DATA_PATH, email, 'emails.db');
-
-// Delete existing DB for a fresh import
-try {
-  unlinkSync(dbPath);
-  console.log(`Deleted ${dbPath}`);
-} catch {
-  console.log('No existing DB to delete');
-}
-
-const db = openEmailDb(email);
-
-console.log(`Importing from ${maildirPath}...`);
-const result = await importMaildir({ maildirPath, emailAccount: email, db, onProgress: (saved, skipped) => {
-  process.stdout.write(`\r  saved ${saved}, skipped ${skipped}`);
-}});
-
-console.log(`\nDone: saved ${result.saved}, skipped ${result.skipped}, errors ${result.errors}`);
-db.close();
diff --git a/src/apps/officer-web/Screens/Dashboard/Settings/IntegrationsSettings/EmailAccounts.tsx b/src/apps/officer-web/Screens/Dashboard/Settings/IntegrationsSettings/EmailAccounts.tsx
index c7bd73dd..77365547 100644
--- a/src/apps/officer-web/Screens/Dashboard/Settings/IntegrationsSettings/EmailAccounts.tsx
+++ b/src/apps/officer-web/Screens/Dashboard/Settings/IntegrationsSettings/EmailAccounts.tsx
@@ -210,7 +210,7 @@ export const EmailAccounts = () => {
                   {account.status === 'queued' && (
                     <span className="text-xs text-duck-dark/50 dark:text-foreground/50">Waiting...</span>
                   )}
-                  {account.status === 'connected' && (
+                  {(account.status === 'connected' || account.status === 'synced') && (
                     <Button
                       type="button"
                       variant="outline"
@@ -224,7 +224,7 @@ export const EmailAccounts = () => {
                       ) : (
                         <RefreshCw className="h-3 w-3" />
                       )}
-                      Initial Sync
+                      Sync
                     </Button>
                   )}
                   <button
diff --git a/src/servers/api/email/accounts.ts b/src/servers/api/email/accounts.ts
index d6f333c4..652232fa 100644
--- a/src/servers/api/email/accounts.ts
+++ b/src/servers/api/email/accounts.ts
@@ -47,7 +47,7 @@ accountsRouter.get('/', async (ctx) => {
       const jobs = await listAllJobs();
       activeJobAccountIds = new Set(
         jobs
-          .filter((j) => j.type === 'email-sync' && (j.status === 'queued' || j.status === 'running'))
+          .filter((j) => (j.type === 'email-sync' || j.type === 'gmail-sync') && (j.status === 'queued' || j.status === 'running'))
           .map((j) => (j.meta as Record<string, unknown> | undefined)?.emailAccountId as number)
           .filter(Boolean),
       );
@@ -148,9 +148,11 @@ accountsRouter.post('/:id/sync', async (ctx) => {
   // Set status immediately so the UI reflects the queued state
   await updateEmailAccountStatus(id, 'queued');
 
+  const jobType = account.provider === 'gmail' ? 'gmail-sync' : 'email-sync';
+
   const job = await enqueueJob({
     lane: 'email',
-    type: 'email-sync',
+    type: jobType,
     userId: user.email,
     meta: {
       emailAccountId: id,
diff --git a/src/servers/data-path.ts b/src/servers/data-path.ts
index f6e5fcc5..cbafeb00 100644
--- a/src/servers/data-path.ts
+++ b/src/servers/data-path.ts
@@ -69,7 +69,6 @@ export const getAttachmentsDir = (email: string, sessionId: string) => join(DATA
 
 export const getUserEmailDir = (email: string) => join(DATA_PATH, email, 'Gmail', 'emails');
 
-export const getMaildirPath = (email: string) => join(DATA_PATH, email, 'Gmail', 'Maildir');
 
 /** Derive a valid Linux username from a display username or email. */
 export const toShellUsername = (username: string, email: string): string => {
diff --git a/src/servers/queue/handlers/gmail-sync.ts b/src/servers/queue/handlers/gmail-sync.ts
index c77fae14..74cde140 100644
--- a/src/servers/queue/handlers/gmail-sync.ts
+++ b/src/servers/queue/handlers/gmail-sync.ts
@@ -1,7 +1,5 @@
 import type { Database } from 'bun:sqlite';
 import { createHash } from 'node:crypto';
-import { join } from 'node:path';
-import { readdir, readFile, writeFile, unlink, mkdir, stat } from 'node:fs/promises';
 import { type JobHandler, PermanentError } from '../types';
 import { registerHandler } from '../handler-registry';
 import { openEmailDb, upsertFromRawEml, setSyncMeta, getSyncMeta } from '../../api/email/email-db';
@@ -12,8 +10,9 @@ import {
   getServerIntegration,
   getDockPaths,
   setDockPaths,
+  updateEmailAccountStatus,
+  getEmailAccount,
 } from 'officerdb';
-import { getMaildirPath } from '@@/data-path';
 import { refreshGoogleAccessToken } from '@@/api/integrations/google-auth';
 
 // ── Credentials ──
@@ -55,40 +54,281 @@ async function loadGmailCredentials(userEmail: string): Promise<GmailCredentials
   return { email: gmailEmail, userId: dbUser.id, appPassword: config.imapAppPassword as string };
 }
 
-// refreshGoogleAccessToken is imported from @@/api/integrations/google-auth
+// ── Stable ID from Message-Id header ──
 
-// ── mbsync config ──
-
-function buildMbsyncConfig(email: string, appPassword: string, maildirPath: string): string {
-  return `IMAPAccount gmail
-Host imap.gmail.com
-Port 993
-User ${email}
-Pass "${appPassword}"
-SSLType IMAPS
-AuthMechs LOGIN
-
-IMAPStore gmail-remote
-Account gmail
-
-MaildirStore gmail-local
-Path ${maildirPath}/
-Inbox ${maildirPath}/INBOX
-SubFolders Verbatim
-
-Channel gmail
-Far :gmail-remote:
-Near :gmail-local:
-Patterns * ![Gmail]/Trash ![Gmail]/Spam ![Gmail]/Bin !"[Gmail]/All Mail" ![Google Mail]/Trash ![Google Mail]/Spam ![Google Mail]/Bin !"[Google Mail]/All Mail"
-Create Near
-Expunge None
-SyncState *
-`;
+function messageIdToStableId(raw: string): string | null {
+  const match = raw.match(/^Message-Id:\s*<?([^>\s]+)>?/im);
+  if (!match?.[1]) return null;
+  return createHash('sha1').update(match[1]).digest('hex').slice(0, 16);
 }
 
-// ── Folder → label mapping ──
+// ── Gmail API label → our label mapping ──
 
-// Strips [Gmail]/ or [Google Mail]/ prefix, returns the suffix (e.g. "Sent Mail")
+const GMAIL_API_LABEL_MAP: Record<string, string> = {
+  INBOX: 'inbox',
+  SENT: 'sent',
+  DRAFT: 'draft',
+  STARRED: 'starred',
+  IMPORTANT: 'important',
+  TRASH: 'trash',
+  SPAM: 'spam',
+  CATEGORY_PROMOTIONS: 'promotions',
+  CATEGORY_SOCIAL: 'social',
+  CATEGORY_UPDATES: 'updates',
+  CATEGORY_FORUMS: 'forums',
+};
+
+const SKIP_LABELS = new Set(['TRASH', 'SPAM', 'DRAFT']);
+
+function gmailApiLabelsToLabels(labelIds: string[]): string[] {
+  const labels: string[] = [];
+  for (const id of labelIds) {
+    const mapped = GMAIL_API_LABEL_MAP[id];
+    if (mapped) {
+      labels.push(mapped);
+    } else if (!id.startsWith('CATEGORY_') && id !== 'UNREAD' && id !== 'IMPORTANT') {
+      // Custom label — use as-is (Gmail API returns label IDs, not names, for custom labels)
+      labels.push(id.toLowerCase());
+    }
+  }
+  return labels;
+}
+
+function shouldSkipMessage(labelIds: string[]): boolean {
+  return labelIds.some((id) => SKIP_LABELS.has(id));
+}
+
+// ── Gmail API helpers ──
+
+const GMAIL_API = 'https://gmail.googleapis.com/gmail/v1/users/me';
+
+type GmailApiResult = { saved: number; skipped: number; errors: number };
+
+async function gmailApiFetch(accessToken: string, path: string, params?: Record<string, string>): Promise<Response> {
+  const url = new URL(`${GMAIL_API}${path}`);
+  if (params) {
+    for (const [k, v] of Object.entries(params)) url.searchParams.set(k, v);
+  }
+  const res = await fetch(url, { headers: { Authorization: `Bearer ${accessToken}` } });
+  return res;
+}
+
+async function getGmailProfile(accessToken: string): Promise<{ historyId: string }> {
+  const res = await gmailApiFetch(accessToken, '/profile');
+  if (!res.ok) throw new Error(`Gmail profile request failed: ${res.status} ${await res.text()}`);
+  const data = (await res.json()) as { historyId: string };
+  return data;
+}
+
+type HistoryMessage = { id: string; threadId: string };
+type HistoryEntry = { messagesAdded?: Array<{ message: HistoryMessage }> };
+type HistoryResponse = { history?: HistoryEntry[]; historyId: string; nextPageToken?: string };
+
+async function getHistoryChanges(
+  accessToken: string,
+  startHistoryId: string,
+): Promise<{ messageIds: string[]; historyId: string }> {
+  const messageIds = new Set<string>();
+  let pageToken: string | undefined;
+  let latestHistoryId = startHistoryId;
+
+  while (true) {
+    const params: Record<string, string> = {
+      startHistoryId,
+      historyTypes: 'messageAdded',
+      maxResults: '500',
+    };
+    if (pageToken) params.pageToken = pageToken;
+
+    const res = await gmailApiFetch(accessToken, '/history', params);
+
+    if (res.status === 404) {
+      // No history — nothing new
+      return { messageIds: [], historyId: latestHistoryId };
+    }
+
+    if (res.status === 410) {
+      // historyId too old — caller should fall back to date-based listing
+      throw new HistoryExpiredError();
+    }
+
+    if (!res.ok) throw new Error(`Gmail history request failed: ${res.status} ${await res.text()}`);
+
+    const data = (await res.json()) as HistoryResponse;
+    latestHistoryId = data.historyId;
+
+    if (data.history) {
+      for (const entry of data.history) {
+        if (entry.messagesAdded) {
+          for (const added of entry.messagesAdded) {
+            messageIds.add(added.message.id);
+          }
+        }
+      }
+    }
+
+    if (!data.nextPageToken) break;
+    pageToken = data.nextPageToken;
+  }
+
+  return { messageIds: [...messageIds], historyId: latestHistoryId };
+}
+
+class HistoryExpiredError extends Error {
+  constructor() {
+    super('Gmail historyId expired');
+  }
+}
+
+type MessageListResponse = { messages?: Array<{ id: string }>; nextPageToken?: string };
+
+async function listMessagesSince(accessToken: string, sinceDate: string): Promise<string[]> {
+  const messageIds: string[] = [];
+  let pageToken: string | undefined;
+
+  while (true) {
+    const params: Record<string, string> = {
+      q: `after:${sinceDate}`,
+      maxResults: '500',
+    };
+    if (pageToken) params.pageToken = pageToken;
+
+    const res = await gmailApiFetch(accessToken, '/messages', params);
+    if (!res.ok) throw new Error(`Gmail messages.list failed: ${res.status} ${await res.text()}`);
+
+    const data = (await res.json()) as MessageListResponse;
+    if (data.messages) {
+      for (const msg of data.messages) messageIds.push(msg.id);
+    }
+
+    if (!data.nextPageToken) break;
+    pageToken = data.nextPageToken;
+  }
+
+  return messageIds;
+}
+
+type GmailMessage = { id: string; labelIds: string[]; raw: string; historyId: string };
+
+async function fetchRawMessage(accessToken: string, messageId: string): Promise<GmailMessage | null> {
+  const res = await gmailApiFetch(accessToken, `/messages/${messageId}`, { format: 'raw' });
+  if (res.status === 404) return null;
+  if (!res.ok) throw new Error(`Gmail messages.get failed: ${res.status} ${await res.text()}`);
+  return (await res.json()) as GmailMessage;
+}
+
+// ── Gmail API sync (for resyncs) ──
+
+type GmailApiSyncParams = {
+  creds: GmailCredentials;
+  db: Database;
+  onProgress?: (saved: number, total: number) => void;
+};
+
+async function gmailApiSync({ creds, db, onProgress }: GmailApiSyncParams): Promise<GmailApiResult> {
+  if (!creds.accessToken) throw new PermanentError('OAuth access token required for Gmail API sync');
+
+  let saved = 0;
+  let skipped = 0;
+  let errors = 0;
+
+  // Load existing IDs for dedup
+  const existingIds = new Set<string>();
+  const rows = db.query('SELECT id FROM emails').all() as Array<{ id: string }>;
+  for (const row of rows) existingIds.add(row.id);
+
+  const storedHistoryId = getSyncMeta(db, 'gmail_history_id');
+
+  let messageIds: string[];
+  let newHistoryId: string;
+
+  if (storedHistoryId) {
+    // Try history-based sync first
+    try {
+      const result = await getHistoryChanges(creds.accessToken, storedHistoryId);
+      messageIds = result.messageIds;
+      newHistoryId = result.historyId;
+      console.log(`[gmail-sync] History returned ${messageIds.length} new message(s)`);
+    } catch (err) {
+      if (err instanceof HistoryExpiredError) {
+        // historyId too old — fall back to date-based listing
+        const lastSyncDate = getSyncMeta(db, 'last_sync_date');
+        const sinceDate = lastSyncDate ?? new Date(Date.now() - 7 * 24 * 60 * 60 * 1000).toISOString().split('T')[0]!;
+        console.log(`[gmail-sync] History expired, falling back to messages since ${sinceDate}`);
+        messageIds = await listMessagesSince(creds.accessToken, sinceDate);
+        const profile = await getGmailProfile(creds.accessToken);
+        newHistoryId = profile.historyId;
+        console.log(`[gmail-sync] Date query returned ${messageIds.length} message(s)`);
+      } else {
+        throw err;
+      }
+    }
+  } else {
+    // No historyId stored — use date-based listing
+    const lastSyncDate = getSyncMeta(db, 'last_sync_date');
+    const sinceDate = lastSyncDate ?? new Date(Date.now() - 7 * 24 * 60 * 60 * 1000).toISOString().split('T')[0]!;
+    console.log(`[gmail-sync] No historyId, listing messages since ${sinceDate}`);
+    messageIds = await listMessagesSince(creds.accessToken, sinceDate);
+    const profile = await getGmailProfile(creds.accessToken);
+    newHistoryId = profile.historyId;
+    console.log(`[gmail-sync] Date query returned ${messageIds.length} message(s)`);
+  }
+
+  // Fetch and store each new message
+  for (let i = 0; i < messageIds.length; i++) {
+    const gmailId = messageIds[i]!;
+
+    try {
+      const msg = await fetchRawMessage(creds.accessToken, gmailId);
+      if (!msg) {
+        skipped++;
+        continue;
+      }
+
+      if (shouldSkipMessage(msg.labelIds ?? [])) {
+        skipped++;
+        continue;
+      }
+
+      // Gmail API returns base64url-encoded raw RFC822
+      const rawBytes = Buffer.from(msg.raw, 'base64url');
+      const raw = rawBytes.toString('utf-8');
+
+      const id = messageIdToStableId(raw);
+      if (!id) {
+        errors++;
+        continue;
+      }
+
+      if (existingIds.has(id)) {
+        skipped++;
+        continue;
+      }
+
+      const labels = gmailApiLabelsToLabels(msg.labelIds ?? []);
+
+      upsertFromRawEml({ db, id, raw, integration: 'gmail', emailAccount: creds.email, labels });
+      existingIds.add(id);
+      saved++;
+
+      if ((saved + skipped) % 50 === 0) {
+        onProgress?.(saved, messageIds.length);
+      }
+    } catch (err) {
+      console.log(`[gmail-sync] Error fetching message ${gmailId}: ${err instanceof Error ? err.message : err}`);
+      errors++;
+    }
+  }
+
+  // Persist new historyId
+  setSyncMeta(db, 'gmail_history_id', newHistoryId);
+
+  return { saved, skipped, errors };
+}
+
+// ── IMAP sync (for first sync) ──
+
+// Folder → label mapping for IMAP
 const GMAIL_PREFIX_RE = /^\[(?:Gmail|Google Mail)\]\//;
 
 function normalizeGmailFolder(folder: string): string {
@@ -108,195 +348,15 @@ const SUFFIX_LABEL_MAP: Record<string, string> = {
 
 function folderToLabel(folder: string): string | null {
   const suffix = normalizeGmailFolder(folder);
-  // If it had a Gmail prefix, check against known suffixes
   if (suffix !== folder) {
     if (SUFFIX_LABEL_MAP[suffix]) return SUFFIX_LABEL_MAP[suffix]!;
     return suffix.toLowerCase();
   }
-  // Non-Gmail folders (INBOX, custom labels)
   if (folder === 'INBOX') return 'inbox';
   return folder.toLowerCase();
 }
 
-// ── Stable ID from Message-Id header ──
-
-function messageIdToStableId(raw: string): string | null {
-  const match = raw.match(/^Message-Id:\s*<?([^>\s]+)>?/im);
-  if (!match?.[1]) return null;
-  return createHash('sha1').update(match[1]).digest('hex').slice(0, 16);
-}
-
-// ── Maildir import ──
-
-type ImportResult = { saved: number; skipped: number; errors: number };
-
-type ImportMaildirParams = {
-  maildirPath: string;
-  emailAccount: string;
-  db: Database;
-  lastSyncAt?: string | null;
-  onProgress?: (saved: number, skipped: number) => void;
-};
-
-export async function importMaildir({
-  maildirPath,
-  emailAccount,
-  db,
-  lastSyncAt,
-  onProgress,
-}: ImportMaildirParams): Promise<ImportResult> {
-  let saved = 0;
-  let skipped = 0;
-  let errors = 0;
-
-  // For incremental syncs, skip files older than last sync (with 60s buffer for clock skew)
-  const mtimeCutoff = lastSyncAt ? new Date(lastSyncAt).getTime() - 60_000 : 0;
-  const isIncremental = mtimeCutoff > 0;
-
-  // Load existing IDs for fast dedup
-  const existingIds = new Set<string>();
-  const rows = db.query('SELECT id FROM emails').all() as Array<{ id: string }>;
-  for (const row of rows) existingIds.add(row.id);
-
-  if (isIncremental) {
-    console.log(
-      `[gmail-sync] Incremental import — only reading files newer than ${new Date(mtimeCutoff).toISOString()}`,
-    );
-  }
-
-  // First pass: collect all message files with their folders to build label map
-  const messageIdLabels = new Map<string, Set<string>>();
-  const messageFiles = new Map<string, string>(); // id → first file path
-
-  // Discover Maildir folders — handles nested [Gmail]/ and [Google Mail]/ structures
-  let topEntries: string[];
-  try {
-    topEntries = await readdir(maildirPath);
-  } catch {
-    console.log('[gmail-sync] No Maildir folders found');
-    return { saved, skipped, errors };
-  }
-
-  const folders: string[] = [];
-  for (const entry of topEntries) {
-    if (entry === '[Gmail]' || entry === '[Google Mail]') {
-      // This is [Gmail] or [Google Mail] — subfolders are one level deeper
-      try {
-        const subs = await readdir(join(maildirPath, entry));
-        for (const sub of subs) folders.push(`${entry}/${sub}`);
-      } catch {
-        // empty
-      }
-    } else {
-      folders.push(entry);
-    }
-  }
-
-  // Process All Mail last so specific-folder labels take priority
-  const isAllMail = (f: string) => normalizeGmailFolder(f) === 'All Mail' && GMAIL_PREFIX_RE.test(f);
-  folders.sort((a, b) => (isAllMail(a) ? 1 : 0) - (isAllMail(b) ? 1 : 0));
-
-  for (const folder of folders) {
-    const label = folderToLabel(folder);
-    if (label === null) continue;
-
-    for (const subdir of ['cur', 'new']) {
-      const dirPath = join(maildirPath, folder, subdir);
-      let files: string[];
-      try {
-        files = await readdir(dirPath);
-      } catch {
-        continue;
-      }
-
-      for (const file of files) {
-        const filePath = join(dirPath, file);
-        try {
-          // Skip files older than last sync for incremental imports
-          if (isIncremental) {
-            const fileStat = await stat(filePath);
-            if (fileStat.mtimeMs < mtimeCutoff) continue;
-          }
-
-          const raw = await readFile(filePath, 'utf-8');
-          const id = messageIdToStableId(raw);
-          if (!id) {
-            errors++;
-            continue;
-          }
-
-          // Track labels — only add "archive" for messages not seen in any specific folder
-          const labels = messageIdLabels.get(id) ?? new Set<string>();
-          if (label !== 'archive' || labels.size === 0) {
-            labels.add(label);
-          }
-          messageIdLabels.set(id, labels);
-
-          // Keep first file path for importing
-          if (!messageFiles.has(id)) {
-            messageFiles.set(id, filePath);
-          }
-        } catch {
-          errors++;
-        }
-      }
-    }
-  }
-
-  // Second pass: import messages that aren't already in DB
-  for (const [id, filePath] of messageFiles) {
-    if (existingIds.has(id)) {
-      skipped++;
-      if ((saved + skipped) % 500 === 0) onProgress?.(saved, skipped);
-      continue;
-    }
-
-    try {
-      const raw = await readFile(filePath, 'utf-8');
-      const labels = Array.from(messageIdLabels.get(id) ?? []);
-
-      upsertFromRawEml({ db, id, raw, integration: 'gmail', emailAccount, labels });
-      existingIds.add(id);
-      saved++;
-
-      if ((saved + skipped) % 100 === 0) {
-        console.log(`[gmail-sync] Import progress: saved ${saved}, skipped ${skipped}, errors ${errors}`);
-        onProgress?.(saved, skipped);
-      }
-    } catch {
-      errors++;
-    }
-  }
-
-  return { saved, skipped, errors };
-}
-
-// ── Maildir stats ──
-
-async function countMaildirFiles(maildirPath: string): Promise<number> {
-  let count = 0;
-  let folders: string[];
-  try {
-    folders = await readdir(maildirPath);
-  } catch {
-    return 0;
-  }
-  for (const folder of folders) {
-    for (const subdir of ['cur', 'new']) {
-      try {
-        const files = await readdir(join(maildirPath, folder, subdir));
-        count += files.length;
-      } catch {
-        continue;
-      }
-    }
-  }
-  return count;
-}
-
-// ── Gmail IMAP label → our label mapping ──
-
-const GMAIL_LABEL_MAP: Record<string, string> = {
+const IMAP_LABEL_MAP: Record<string, string> = {
   '\\Inbox': 'inbox',
   '\\Sent': 'sent',
   '\\Drafts': 'draft',
@@ -307,26 +367,22 @@ const GMAIL_LABEL_MAP: Record<string, string> = {
   '\\Junk': 'spam',
 };
 
-function gmailLabelsToLabels(gmailLabels: Set<string>): string[] {
+function imapLabelsToLabels(gmailLabels: Set<string>): string[] {
   const labels: string[] = [];
   for (const gl of gmailLabels) {
-    const mapped = GMAIL_LABEL_MAP[gl];
+    const mapped = IMAP_LABEL_MAP[gl];
     if (mapped) {
       labels.push(mapped);
     } else if (!gl.startsWith('\\')) {
-      // Custom label — lowercase it
       labels.push(gl.toLowerCase());
     }
   }
-  // If only "archive" and no specific folder, keep it; otherwise drop "archive"
   if (labels.length > 1 && labels.includes('archive')) {
     return labels.filter((l) => l !== 'archive');
   }
   return labels;
 }
 
-// ── IMAP special-use folders to skip ──
-
 const SKIP_SPECIAL_USE = new Set(['\\Trash', '\\Junk', '\\All']);
 
 function shouldSkipFolder(folder: { specialUse?: string; path: string; flags: Set<string> }): boolean {
@@ -336,25 +392,22 @@ function shouldSkipFolder(folder: { specialUse?: string; path: string; flags: Se
   return norm === 'All Mail' || norm === 'Trash' || norm === 'Spam' || norm === 'Bin';
 }
 
-// ── Incremental IMAP sync ──
-
-type IncrementalSyncParams = {
+type ImapSyncParams = {
   creds: GmailCredentials;
   db: Database;
   onProgress?: (fetched: number, folder: string) => void;
 };
 
-type IncrementalSyncResult = { saved: number; skipped: number; errors: number };
+type SyncResult = { saved: number; skipped: number; errors: number };
 
-async function incrementalImapSync({ creds, db, onProgress }: IncrementalSyncParams): Promise<IncrementalSyncResult> {
+async function imapFullSync({ creds, db, onProgress }: ImapSyncParams): Promise<SyncResult> {
   const { ImapFlow } = await import('imapflow');
 
-  // Determine auth method: prefer OAuth, fall back to app password
   const auth: { user: string; pass?: string; accessToken?: string } = { user: creds.email };
-  if (creds.accessToken) {
-    auth.accessToken = creds.accessToken;
-  } else if (creds.appPassword) {
+  if (creds.appPassword) {
     auth.pass = creds.appPassword;
+  } else if (creds.accessToken) {
+    auth.accessToken = creds.accessToken;
   } else {
     throw new PermanentError('No authentication method available for IMAP');
   }
@@ -373,17 +426,14 @@ async function incrementalImapSync({ creds, db, onProgress }: IncrementalSyncPar
 
   try {
     await client.connect();
-    console.log('[gmail-sync] Incremental IMAP connected');
+    console.log('[gmail-sync] IMAP connected for full sync');
 
-    // Get all folders with status in a single LIST command
     const folders = await client.list({ statusQuery: { uidNext: true, uidValidity: true } });
 
-    // Load existing IDs for dedup
     const existingIds = new Set<string>();
     const rows = db.query('SELECT id FROM emails').all() as Array<{ id: string }>;
     for (const row of rows) existingIds.add(row.id);
 
-    // Filter to only folders with new messages
     const foldersToSync: typeof folders = [];
     for (const folder of folders) {
       if (shouldSkipFolder(folder)) continue;
@@ -400,17 +450,12 @@ async function incrementalImapSync({ creds, db, onProgress }: IncrementalSyncPar
         storedUidValidity && uidValidity === storedUidValidity && storedLastUid ? parseInt(storedLastUid, 10) : 0;
 
       if (uidValidity) setSyncMeta(db, uidValidityKey, uidValidity);
-
-      if (lastUid > 0 && uidNext <= lastUid + 1) continue; // no new messages
-
-      if (storedUidValidity && uidValidity && storedUidValidity !== uidValidity) {
-        console.log(`[gmail-sync] UIDVALIDITY changed for ${folderPath} — will re-scan`);
-      }
+      if (lastUid > 0 && uidNext <= lastUid + 1) continue;
 
       foldersToSync.push(folder);
     }
 
-    console.log(`[gmail-sync] ${foldersToSync.length} folder(s) with new messages`);
+    console.log(`[gmail-sync] ${foldersToSync.length} folder(s) to sync`);
 
     for (const folder of foldersToSync) {
       const folderPath = folder.path;
@@ -419,7 +464,6 @@ async function incrementalImapSync({ creds, db, onProgress }: IncrementalSyncPar
       const storedUidValidity = getSyncMeta(db, uidValidityKey);
       const storedLastUid = getSyncMeta(db, lastUidKey);
 
-      // Open folder and fetch new messages
       let lock;
       try {
         lock = await client.getMailboxLock(folderPath);
@@ -466,10 +510,8 @@ async function incrementalImapSync({ creds, db, onProgress }: IncrementalSyncPar
               continue;
             }
 
-            // Gmail X-GM-EXT-1 labels don't include folder membership (e.g. \Inbox),
-            // so always use the folder we're fetching from as the base label
             const folderLabel = folderToLabel(folderPath);
-            const gmailLabels = msg.labels ? gmailLabelsToLabels(msg.labels) : [];
+            const gmailLabels = msg.labels ? imapLabelsToLabels(msg.labels) : [];
             const labels = folderLabel ? [...new Set([folderLabel, ...gmailLabels])] : gmailLabels;
 
             try {
@@ -518,27 +560,43 @@ const gmailSyncHandler: JobHandler = {
       name: 'Verify credentials',
       run: async (ctx) => {
         const creds = await loadGmailCredentials(ctx.job.userId);
+        const emailAccountId = (ctx.meta as Record<string, unknown>).emailAccountId as number | undefined;
 
-        // Determine sync mode: incremental if we have a previous sync
+        // Determine sync mode — check SQLite first, fall back to PostgreSQL syncMeta
         const db = openEmailDb(ctx.job.userId);
+        let lastSyncAt: string | null = null;
         try {
-          const lastSyncAt = getSyncMeta(db, 'last_sync_at');
-          ctx.meta.isIncremental = !!lastSyncAt;
+          lastSyncAt = getSyncMeta(db, 'last_sync_at');
+          if (!lastSyncAt && emailAccountId) {
+            const pgAccount = await getEmailAccount(emailAccountId);
+            const pgMeta = pgAccount?.syncMeta as Record<string, string> | null;
+            if (pgMeta?.last_sync_at) {
+              lastSyncAt = pgMeta.last_sync_at;
+              // Backfill SQLite so future checks don't need PostgreSQL
+              setSyncMeta(db, 'last_sync_at', lastSyncAt);
+              if (pgMeta.last_sync_date) setSyncMeta(db, 'last_sync_date', pgMeta.last_sync_date);
+            }
+          }
+          ctx.meta.isFirstSync = !lastSyncAt;
         } finally {
           db.close();
         }
 
-        // For incremental sync with OAuth, refresh token if expired
-        if (ctx.meta.isIncremental && creds.accessToken && creds.refreshToken) {
+        if (emailAccountId) {
+          await updateEmailAccountStatus(emailAccountId, 'syncing');
+          ctx.meta.emailAccountId = emailAccountId;
+        }
+
+        // For API resyncs, refresh OAuth token if expired
+        if (!ctx.meta.isFirstSync && creds.accessToken && creds.refreshToken) {
           const tokenExpired = !creds.expiresAt || creds.expiresAt < Date.now() + 60_000;
           if (tokenExpired) {
-            console.log('[gmail-sync] Refreshing OAuth token for incremental sync');
+            console.log('[gmail-sync] Refreshing OAuth token');
             try {
               const refreshed = await refreshGoogleAccessToken(creds.refreshToken);
               creds.accessToken = refreshed.accessToken;
               creds.expiresAt = refreshed.expiresAt;
 
-              // Persist refreshed token
               const userGoogle = await getUserIntegration(creds.userId, 'google');
               const existingConfig = (userGoogle?.config as Record<string, unknown>) ?? {};
               const serverGoogle = await getServerIntegration('google');
@@ -549,39 +607,35 @@ const gmailSyncHandler: JobHandler = {
                 config: { ...existingConfig, accessToken: refreshed.accessToken, expiresAt: refreshed.expiresAt },
               });
             } catch (err) {
-              console.log(`[gmail-sync] OAuth refresh failed, will fall back to app password: ${err}`);
-              // Clear OAuth so we fall back to app password
-              creds.accessToken = undefined;
-              creds.refreshToken = undefined;
+              throw new PermanentError(`OAuth refresh failed — reconnect Google in Settings: ${err}`);
             }
           }
         }
 
-        ctx.meta.creds = creds;
-        ctx.meta.email = creds.email;
-        ctx.meta.appPassword = creds.appPassword;
-
-        if (ctx.meta.isIncremental) {
-          console.log(`[gmail-sync] Incremental sync mode (${creds.accessToken ? 'OAuth' : 'App Password'})`);
-        } else {
-          console.log('[gmail-sync] Full sync mode (mbsync)');
-          if (!creds.appPassword) {
-            throw new PermanentError('Gmail App Password required for initial sync');
-          }
+        if (!ctx.meta.isFirstSync && !creds.accessToken) {
+          throw new PermanentError('OAuth not configured — connect Google in Settings → Integrations for resyncs');
         }
+
+        ctx.meta.creds = creds;
+        console.log(
+          `[gmail-sync] ${ctx.meta.isFirstSync ? 'First sync (IMAP)' : 'Resync (Gmail API)'} — ${creds.accessToken ? 'OAuth' : 'App Password'}`,
+        );
       },
     },
     {
       name: 'Sync emails',
       run: async (ctx) => {
-        if (ctx.meta.isIncremental) {
-          // ── Incremental: direct IMAP via imapflow ──
-          const creds = ctx.meta.creds as GmailCredentials;
-          await ctx.updateProgress({ current: 0, total: 0, label: 'Connecting to Gmail...' });
+        const creds = ctx.meta.creds as GmailCredentials;
 
-          const db = openEmailDb(ctx.job.userId);
-          try {
-            const result = await incrementalImapSync({
+        const db = openEmailDb(ctx.job.userId);
+        try {
+          let result: SyncResult;
+
+          if (ctx.meta.isFirstSync) {
+            // First sync: IMAP with app password
+            await ctx.updateProgress({ current: 0, total: 0, label: 'Connecting to Gmail (IMAP)...' });
+
+            result = await imapFullSync({
               creds,
               db,
               onProgress: (fetched, folder) => {
@@ -589,200 +643,71 @@ const gmailSyncHandler: JobHandler = {
               },
             });
 
-            console.log(
-              `[gmail-sync] Incremental sync done: saved ${result.saved}, skipped ${result.skipped}, errors ${result.errors}`,
-            );
-
-            setSyncMeta(db, 'last_sync_date', new Date().toISOString().split('T')[0]!);
-            setSyncMeta(db, 'last_sync_at', new Date().toISOString());
-
-            ctx.meta.syncResult = result;
-            await ctx.updateProgress({ current: 1, total: 1, label: `Done — ${result.saved} new emails` });
-          } finally {
-            db.close();
-          }
-        } else {
-          // ── Full sync: mbsync ──
-          const email = ctx.meta.email as string;
-          const appPassword = ctx.meta.appPassword as string;
-          const maildirPath = getMaildirPath(ctx.job.userId);
-
-          await mkdir(maildirPath, { recursive: true });
-
-          const configPath = join(maildirPath, '.mbsyncrc');
-          const config = buildMbsyncConfig(email, appPassword, maildirPath);
-          await writeFile(configPath, config, { mode: 0o600 });
-
-          await ctx.updateProgress({ current: 0, total: 0, label: 'Running mbsync...' });
-
-          try {
-            let proc: ReturnType<typeof Bun.spawn>;
-            try {
-              proc = Bun.spawn(['mbsync', '-c', configPath, '-a'], {
-                stdout: 'pipe',
-                stderr: 'pipe',
-              });
-            } catch (spawnErr) {
-              const msg = spawnErr instanceof Error ? spawnErr.message : String(spawnErr);
-              throw new PermanentError(`Failed to start mbsync: ${msg}`);
+            // Seed historyId for future API syncs
+            if (creds.accessToken) {
+              try {
+                const profile = await getGmailProfile(creds.accessToken);
+                setSyncMeta(db, 'gmail_history_id', profile.historyId);
+                console.log(`[gmail-sync] Seeded historyId: ${profile.historyId}`);
+              } catch (err) {
+                console.log(`[gmail-sync] Could not seed historyId: ${err}`);
+              }
             }
+          } else {
+            // Resync: Gmail API with OAuth
+            await ctx.updateProgress({ current: 0, total: 0, label: 'Checking for new emails...' });
 
-            let emailCount = 0;
-            let counting = true;
-            const countLoop = (async () => {
-              while (counting) {
-                await new Promise((r) => setTimeout(r, 3000));
-                if (!counting) break;
-                emailCount = await countMaildirFiles(maildirPath);
-                ctx.updateProgress({
-                  current: emailCount,
-                  total: 0,
-                  label: `Downloading — ${emailCount.toLocaleString()} emails`,
-                });
-              }
-            })();
-
-            let stderrBuf = '';
-            const reader = (proc.stderr as ReadableStream<Uint8Array>).getReader();
-            const decoder = new TextDecoder();
-            const readLoop = (async () => {
-              while (true) {
-                const { done, value } = await reader.read();
-                if (done) break;
-                const chunk = decoder.decode(value, { stream: true });
-                stderrBuf += chunk;
-                const lines = chunk.split('\n');
-                for (const line of lines) {
-                  const trimmed = line.trim();
-                  if (trimmed) console.log(`[gmail-sync] mbsync: ${trimmed}`);
-                }
-              }
-            })();
-
-            const exitCode = await proc.exited;
-            counting = false;
-            await readLoop;
-            await countLoop;
-
-            if (exitCode !== 0) {
-              const isOverquota = stderrBuf.includes('OVERQUOTA');
-              const isAuthFail =
-                stderrBuf.includes('AUTHENTICATIONFAILED') || stderrBuf.includes('Invalid credentials');
-
-              if (isOverquota) {
-                const emailCount = await countMaildirFiles(maildirPath);
-                console.log(`[gmail-sync] Gmail OVERQUOTA — proceeding to import ${emailCount} downloaded emails`);
-                ctx.meta.gmailSyncPartial = true;
-                ctx.meta.gmailSyncEmailCount = emailCount;
-              } else {
-                console.error(`[gmail-sync] mbsync failed`);
-                if (isAuthFail) {
-                  const emailCount = await countMaildirFiles(maildirPath);
-                  ctx.meta.gmailSyncRecoverable = true;
-                  ctx.meta.gmailSyncEmailCount = emailCount;
-                  ctx.meta.gmailSyncIsAuthFail = true;
-                  throw new PermanentError(`Authentication failed — check your App Password`);
-                }
-                throw new Error(`mbsync exited with code ${exitCode}: ${stderrBuf.slice(-500)}`);
-              }
-            } else {
-              emailCount = await countMaildirFiles(maildirPath);
-              console.log(`[gmail-sync] mbsync completed successfully — ${emailCount} emails`);
-              await ctx.updateProgress({
-                current: emailCount,
-                total: emailCount,
-                label: `Download complete — ${emailCount.toLocaleString()} emails`,
-              });
-            }
-          } finally {
-            await unlink(configPath).catch(() => {});
+            result = await gmailApiSync({
+              creds,
+              db,
+              onProgress: (saved, total) => {
+                ctx.updateProgress({ current: saved, total, label: `Fetching new emails (${saved}/${total})...` });
+              },
+            });
           }
-        }
-      },
-    },
-    {
-      name: 'Import to database',
-      run: async (ctx) => {
-        // Incremental sync already imported in the previous step
-        if (ctx.meta.isIncremental) {
-          const result = ctx.meta.syncResult as IncrementalSyncResult | undefined;
-
-          // Auto-add /email to dock
-          if (result && result.saved > 0) {
-            try {
-              const dbUser = await getUserByEmail(ctx.job.userId);
-              if (dbUser) {
-                const paths = await getDockPaths(dbUser.id);
-                if (!paths) {
-                  const defaults = ['/', '/files', '/automation', '/projects', '/dashboards', '/chat'];
-                  await setDockPaths(dbUser.id, [...defaults, '/email']);
-                } else if (!paths.includes('/email')) {
-                  await setDockPaths(dbUser.id, [...paths, '/email']);
-                }
-              }
-            } catch {
-              // Non-fatal
-            }
-          }
-
-          await ctx.updateProgress({ current: 1, total: 1, label: `Done — ${result?.saved ?? 0} new emails` });
-          return;
-        }
-
-        // Full sync: import from Maildir
-        const emailAccount = ctx.meta.email as string;
-        const maildirPath = getMaildirPath(ctx.job.userId);
-
-        await ctx.updateProgress({ current: 0, total: 0, label: 'Importing emails...' });
-
-        const db = openEmailDb(ctx.job.userId);
-        try {
-          const lastSyncAt = getSyncMeta(db, 'last_sync_at');
-          const result = await importMaildir({
-            maildirPath,
-            emailAccount,
-            db,
-            lastSyncAt,
-            onProgress: (saved, skipped) => {
-              ctx.updateProgress({
-                current: saved + skipped,
-                total: 0,
-                label: `Saved ${saved.toLocaleString()}, skipped ${skipped.toLocaleString()}`,
-              });
-            },
-          });
 
           console.log(
-            `[gmail-sync] Import done: saved ${result.saved}, skipped ${result.skipped}, errors ${result.errors}`,
+            `[gmail-sync] Done: saved ${result.saved}, skipped ${result.skipped}, errors ${result.errors}`,
           );
 
           setSyncMeta(db, 'last_sync_date', new Date().toISOString().split('T')[0]!);
           setSyncMeta(db, 'last_sync_at', new Date().toISOString());
 
-          // Auto-add /email to dock if not already present
-          if (result.saved > 0) {
-            try {
-              const dbUser = await getUserByEmail(ctx.job.userId);
-              if (dbUser) {
-                const paths = await getDockPaths(dbUser.id);
-                if (!paths) {
-                  const defaults = ['/', '/files', '/automation', '/projects', '/dashboards', '/chat'];
-                  await setDockPaths(dbUser.id, [...defaults, '/email']);
-                } else if (!paths.includes('/email')) {
-                  await setDockPaths(dbUser.id, [...paths, '/email']);
-                }
-              }
-            } catch {
-              // Non-fatal — dock update is best-effort
-            }
-          }
-
+          ctx.meta.syncResult = result;
           await ctx.updateProgress({ current: 1, total: 1, label: `Done — ${result.saved} new emails` });
         } finally {
           db.close();
         }
       },
     },
+    {
+      name: 'Finalize',
+      run: async (ctx) => {
+        const result = ctx.meta.syncResult as SyncResult | undefined;
+        const emailAccountId = ctx.meta.emailAccountId as number | undefined;
+
+        if (emailAccountId) {
+          await updateEmailAccountStatus(emailAccountId, 'synced');
+        }
+
+        if (result && result.saved > 0) {
+          try {
+            const dbUser = await getUserByEmail(ctx.job.userId);
+            if (dbUser) {
+              const paths = await getDockPaths(dbUser.id);
+              if (!paths) {
+                const defaults = ['/', '/files', '/automation', '/projects', '/dashboards', '/chat'];
+                await setDockPaths(dbUser.id, [...defaults, '/email']);
+              } else if (!paths.includes('/email')) {
+                await setDockPaths(dbUser.id, [...paths, '/email']);
+              }
+            }
+          } catch {
+            // Non-fatal
+          }
+        }
+      },
+    },
   ],
 };