Fix: IMAP over SSL connected without TLS; never lose a sent message's copy

v1.3.26's IMAP4_SSL subclass put its create_client ahead of aioimaplib's,
which is where the TLS context is made — so port 993 got plain TCP, the
server waited for a handshake, and every SSL account timed out ("Can't
reach the mail server"). The context is now made in our create_client too,
and a test checks an SSL client really gets one (it fails without the fix).

With IMAP down, a send could still be delivered by SMTP while filing its copy
in Sent failed — the send then counted as done and the copy was lost. The
copy is now kept and filed by file_sent_copy_job, retried (arq Retry) for
about 24 hours, then shown in Sent as usual.

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

backend/app/outbox/jobs.py

@@ -20,6 +20,7 @@ from sqlalchemy.ext.asyncio import AsyncSession
 
 from app.db import session_scope
 from app.events import get_event_bus
+from app.indexer import blobstore
 from app.indexer.indexer import persist_message
 from app.models import Account, Draft, KnownRecipient, Mailbox, Message, Outbox
 from app.outbox.attachments import load_attachments
@@ -28,6 +29,7 @@ from app.outbox.service import delete_mirrored_draft_row
 from app.providers.base import RemoteMessage
 from app.queue import enqueue_job
 from app.search.factory import get_search_backend
+from app.sync.actions import _retry_later
 from app.sync.health import is_temporary
 from app.sync.provider_factory import build_provider
 
@@ -167,6 +169,37 @@ async def _send_failed(
         )
 
 
+async def file_sent_copy_job(ctx: dict[str, Any], account_id: str, user_id: str, sha: str) -> None:
+    """File a sent message's copy in Sent, after the send itself succeeded but
+    the IMAP server could not be reached. Retried (arq Retry) for ~24 hours."""
+    uid = uuid.UUID(user_id)
+    async with session_scope() as session:
+        account = await session.get(Account, uuid.UUID(account_id))
+        if account is None:
+            return
+        sent_path = await session.scalar(
+            select(Mailbox.path).where(
+                Mailbox.account_id == account.id, Mailbox.special_use == "sent"
+            )
+        )
+    if not sent_path:
+        return
+    raw = blobstore.load(uid, sha)
+    provider = build_provider(account)
+    try:
+        appended_uid = await provider.append(sent_path, raw, frozenset({"\\Seen"}))
+    except Exception as exc:
+        retry = _retry_later(ctx, exc)
+        if retry is not None:
+            raise retry from exc
+        logger.error("could not file a sent message in Sent (blob %s): %s", sha, exc)
+        return
+    finally:
+        await provider.close()
+    await _persist_sent_copy(uid, account, raw, appended_uid)
+    logger.info("filed a sent message in Sent for account %s", account_id)
+
+
 async def send_job(ctx: dict[str, Any], outbox_id: str) -> None:
     """Send a queued message unless it was cancelled during the undo window.
 
@@ -229,16 +262,22 @@ async def send_job(ctx: dict[str, Any], outbox_id: str) -> None:
         except Exception as exc:  # noqa: BLE001 - retry or record; the draft is kept
             await _send_failed(oid, user_id, subject, exc)
             return
-        # Delivered. Filing it is housekeeping: if the IMAP server is not there
-        # right now, the send still succeeded (the Sent poll files it later).
-        try:
+        # Delivered. If filing the copy in Sent fails (the IMAP server is not
+        # there right now), the send still succeeded — and the copy must not be
+        # lost: it is kept and filed later by file_sent_copy_job.
         if sent_path and not gmail:
+            try:
                 appended_uid = await provider.append(sent_path, sent_raw, frozenset({"\\Seen"}))
+            except Exception as exc:  # noqa: BLE001
+                logger.warning("outbox %s sent; filing it in Sent failed, will retry: %s", oid, exc)
+                sha = blobstore.store(user_id, sent_raw)
+                await enqueue_job("file_sent_copy_job", str(account_obj.id), str(user_id), sha)
         # Remove the mirrored Drafts-folder copy now that it has been sent.
         if drafts_path and draft_imap_uid:
+            try:
                 await provider.delete_messages(drafts_path, [draft_imap_uid])
             except Exception as exc:  # noqa: BLE001
-            logger.warning("outbox %s sent, but filing it on the server failed: %s", oid, exc)
+                logger.warning("outbox %s sent; removing its Drafts copy failed: %s", oid, exc)
     finally:
         await provider.close()
 

backend/app/providers/imap_smtp/provider.py

@@ -11,6 +11,7 @@ from __future__ import annotations
 import asyncio
 import contextlib
 import re
+import ssl
 from collections.abc import AsyncIterator
 from dataclasses import dataclass
 from datetime import date
@@ -67,6 +68,11 @@ class _KeepConnectTask:
     def create_client(  # type: ignore[no-untyped-def]
         self, host, port, loop, conn_lost_cb=None, ssl_context=None
     ) -> None:
+        # This replaces IMAP4_SSL.create_client too (it comes first in the MRO),
+        # so do its one job here: without a context the connection is plain
+        # TCP to port 993, and the server just waits for a TLS handshake.
+        if ssl_context is None and isinstance(self, aioimaplib.IMAP4_SSL):
+            ssl_context = ssl.create_default_context(ssl.Purpose.SERVER_AUTH)
         local_loop = loop if loop is not None else asyncio.get_running_loop()
         self.protocol = aioimaplib.IMAP4ClientProtocol(local_loop, conn_lost_cb)
         self.connect_task = local_loop.create_task(

backend/tests/outbox/test_outbox.py

@@ -11,7 +11,9 @@ from datetime import UTC, datetime, timedelta
 from email.policy import default as default_policy
 
 import httpx
+import pytest
 import pytest_asyncio
+from arq import Retry
 from httpx import ASGITransport
 from sqlalchemy import delete, select
 from sqlalchemy.ext.asyncio import AsyncSession, async_sessionmaker, create_async_engine
@@ -615,6 +617,24 @@ async def test_delivered_but_not_filed_counts_as_sent(ctx: Ctx, monkeypatch) ->
     await outbox_jobs.send_job({"job_try": 1}, str(oid))
     assert (await _outbox(ctx, oid)).state == "sent" and len(fake.sent) == 1
 
+    # The copy is not lost: kept, and a job files it once IMAP answers again.
+    args, _ = ctx.enqueued[-1]
+    assert args[0] == "file_sent_copy_job"
+    _, account_id, user_id, sha = args
+    with pytest.raises(Retry):  # still unreachable: tried again later
+        await outbox_jobs.file_sent_copy_job({"job_try": 1}, account_id, user_id, sha)
+    fake.append_error = None
+    await outbox_jobs.file_sent_copy_job({"job_try": 2}, account_id, user_id, sha)
+    assert fake.appended == ["Sent"]
+    ctx.session.expunge_all()
+    async with session_scope() as verify:
+        sent_msg = await verify.scalar(
+            select(Message)
+            .join(Mailbox, Mailbox.id == Message.mailbox_id)
+            .where(Mailbox.account_id == ctx.account_id, Mailbox.special_use == "sent")
+        )
+        assert sent_msg is not None and sent_msg.subject == "Re: Hi"
+
 
 async def test_two_jobs_for_one_send_send_once(ctx: Ctx, monkeypatch) -> None:  # type: ignore[no-untyped-def]
     oid = await _make_outbox(ctx, state="retrying")

backend/tests/sync/test_account_health.py

@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import contextlib
 import uuid
 from collections.abc import AsyncIterator
 
@@ -125,3 +126,27 @@ async def test_refused_sign_in_stops_syncing(account_id: uuid.UUID) -> None:
     await health.failed(ProviderAuthError("AUTHENTICATIONFAILED"))
     account = await _account(account_id)
     assert account.state == "auth_failed" and "AUTHENTICATIONFAILED" in account.state_detail
+
+
+async def test_ssl_connections_really_use_tls(monkeypatch) -> None:  # type: ignore[no-untyped-def]
+    """Regression (v1.3.26): our IMAP4_SSL subclass skipped aioimaplib's TLS
+    setup, so port 993 got plain TCP and every account timed out."""
+    import asyncio
+    import ssl
+
+    from app.providers.imap_smtp.provider import _IMAP4, _IMAP4_SSL
+
+    seen: list[object] = []
+    loop = asyncio.get_running_loop()
+
+    async def fake_create_connection(factory, host, port, ssl=None):  # type: ignore[no-untyped-def]
+        seen.append(ssl)
+        raise ConnectionRefusedError
+
+    monkeypatch.setattr(loop, "create_connection", fake_create_connection)
+    for cls in (_IMAP4_SSL, _IMAP4):
+        client = cls(host="imap.example.com", port=993, timeout=1)
+        with contextlib.suppress(ConnectionRefusedError):
+            await client.connect_task
+    assert isinstance(seen[0], ssl.SSLContext)  # SSL: a TLS context
+    assert seen[1] is None  # plain / STARTTLS: none up front

backend/workers/worker.py

@@ -15,7 +15,7 @@ from typing import Any
 from arq import func
 
 from app.outbox.draft_sync import push_draft_to_imap_job, remove_imap_draft_job
-from app.outbox.jobs import send_job
+from app.outbox.jobs import file_sent_copy_job, send_job
 from app.sync.actions import (
     ACTION_MAX_TRIES,
     delete_thread_job,
@@ -48,6 +48,7 @@ _RETRYING_ACTIONS: list[Any] = [
     restore_thread_job,
     delete_thread_job,
     empty_folder_job,
+    file_sent_copy_job,
 ]
 
 INTERACTIVE_FUNCTIONS: list[Any] = [