fix(reminders): support OAuth SMTP accounts (#5649)

routes/note/note_routes.py

@@ -301,7 +301,7 @@ async def dispatch_reminder(
     email_error = ""
     if channel == "email":
         try:
-            from routes.email_routes import _get_email_config
+            from routes.email_routes import _get_email_config, _smtp_ready
             from email.mime.text import MIMEText
             from email.mime.multipart import MIMEMultipart
             from datetime import datetime as _dt
@@ -311,7 +311,7 @@ async def dispatch_reminder(
             # account when no explicit choice is saved.
             _acc_id = (settings.get("reminder_email_account_id") or "").strip() or None
             cfg = _get_email_config(account_id=_acc_id, owner=owner or "")
-            if not (cfg.get("smtp_host") and cfg.get("smtp_user") and cfg.get("smtp_password")):
+            if not _smtp_ready(cfg):
                 try:
                     from core.database import SessionLocal as _SL, EmailAccount as _EA
                     from sqlalchemy import and_, or_
@@ -324,7 +324,7 @@ async def dispatch_reminder(
                             q = q.filter(or_(_EA.owner == owner, and_(unowned, same_mailbox)))
                         for row in q.order_by(_EA.is_default.desc(), _EA.created_at.asc()).all():
                             trial = _get_email_config(account_id=row.id, owner=owner or "")
-                            if trial.get("smtp_host") and trial.get("smtp_user") and trial.get("smtp_password"):
+                            if _smtp_ready(trial):
                                 cfg = trial
                                 break
                     finally:
@@ -347,8 +347,8 @@ async def dispatch_reminder(
                 missing.append("SMTP host")
             if not cfg.get("smtp_user"):
                 missing.append("SMTP user")
-            if not cfg.get("smtp_password"):
+            if not (cfg.get("smtp_password") or cfg.get("oauth_provider")):
-                missing.append("SMTP password")
+                missing.append("SMTP credentials")
             if not from_addr:
                 missing.append("from address")
             if not recipient:

static/js/settings.js

@@ -2412,11 +2412,16 @@ async function initReminderSettings() {
   // what the Integrations panel manages. Treat the email channel as
   // configured if there's at least one account with SMTP set.
   let emailAccounts = [];
+  const smtpAccountReady = (account) => !!(
+    account.smtp_host
+    && account.smtp_user
+    && (account.has_smtp_password || account.oauth_provider === 'google')
+  );
   try {
     const res = await fetch('/api/email/accounts', { credentials: 'same-origin' });
     if (res.ok) {
       const d = await res.json();
-      emailAccounts = (d.accounts || []).filter(a => a.smtp_host && a.smtp_user && a.has_smtp_password);
+      emailAccounts = (d.accounts || []).filter(smtpAccountReady);
     }
   } catch (_) {}
   let smtpConfigured = emailAccounts.length > 0;
@@ -2520,7 +2525,7 @@ async function initReminderSettings() {
       const res = await fetch('/api/email/accounts', { credentials: 'same-origin' });
       if (res.ok) {
         const d = await res.json();
-        emailAccounts = (d.accounts || []).filter(a => a.smtp_host && a.smtp_user && a.has_smtp_password);
+        emailAccounts = (d.accounts || []).filter(smtpAccountReady);
       }
     } catch (_) {}
     smtpConfigured = emailAccounts.length > 0;

tests/test_note_reminder_email_oauth.py

@@ -0,0 +1,62 @@
+"""Regression coverage for passwordless Google OAuth reminder senders."""
+
+import asyncio
+from pathlib import Path
+from unittest.mock import patch
+
+from routes.note_routes import dispatch_reminder
+
+
+_REPO = Path(__file__).resolve().parents[1]
+
+
+def test_dispatch_reminder_sends_with_google_oauth_without_smtp_password():
+    cfg = {
+        "account_name": "Workspace",
+        "smtp_host": "smtp.gmail.com",
+        "smtp_port": 587,
+        "smtp_security": "starttls",
+        "smtp_user": "alice@example.edu",
+        "smtp_password": "",
+        "from_address": "alice@example.edu",
+        "oauth_provider": "google",
+    }
+    sent = []
+
+    def fake_send(actual_cfg, sender, recipients, message):
+        sent.append((actual_cfg, sender, recipients, message))
+
+    with (
+        patch("src.settings.load_settings", return_value={}),
+        patch("routes.email_routes._get_email_config", return_value=cfg),
+        patch("routes.email_helpers._send_smtp_message", side_effect=fake_send),
+        patch("core.database.SessionLocal", side_effect=AssertionError("fallback lookup is not needed")),
+    ):
+        result = asyncio.run(dispatch_reminder(
+            "Reminder: Submit report",
+            "The report is due today.",
+            note_id="",
+            owner="alice@example.edu",
+            queue_browser=False,
+            settings_override={
+                "reminder_channel": "email",
+                "reminder_llm_synthesis": False,
+            },
+        ))
+
+    assert result["email_sent"] is True
+    assert result["email_error"] == ""
+    assert len(sent) == 1
+    actual_cfg, sender, recipients, message = sent[0]
+    assert actual_cfg is cfg
+    assert sender == "alice@example.edu"
+    assert recipients == ["alice@example.edu"]
+    assert "Subject: Reminder (Odysseus): Submit report" in message
+
+
+def test_reminder_settings_offer_oauth_smtp_accounts():
+    source = (_REPO / "static" / "js" / "settings.js").read_text(encoding="utf-8")
+    helper = source[source.index("const smtpAccountReady"):source.index("const smtpAccountReady") + 260]
+
+    assert "account.has_smtp_password || account.oauth_provider === 'google'" in helper
+    assert source.count(".filter(smtpAccountReady)") == 2