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