webmail-client/backend/tests/sync/test_account_health.py

"""An account whose mail server is unreachable, or refuses the password."""

from __future__ import annotations

import contextlib
import uuid
from collections.abc import AsyncIterator

import aiosmtplib
import pytest_asyncio
from aioimaplib import aioimaplib
from sqlalchemy import delete

from app.db import session_scope
from app.identity.passwords import hash_password
from app.models import Account, User
from app.providers.base import (
    ProviderAuthError,
    ProviderConnectError,
    ProviderRejectedError,
)
from app.providers.imap_smtp.provider import _smtp_error
from app.sync.health import AUTH_GIVE_UP_AFTER, UNREACHABLE_AFTER, AccountHealth, is_temporary


@pytest_asyncio.fixture
async def account_id() -> AsyncIterator[uuid.UUID]:
    async with session_scope() as session:
        user = User(
            handle=f"hl{uuid.uuid4().hex[:8]}@test.local", password_hash=hash_password("pw")
        )
        session.add(user)
        await session.flush()
        account = Account(
            user_id=user.id,
            email="me@example.com",
            imap_config={"host": "imap.example.com", "port": 993, "tls": "ssl"},
            smtp_config={"host": "smtp.example.com", "port": 465, "tls": "ssl"},
            secret_ct=b"",
            discovery_src="manual",
            state="live",
        )
        session.add(account)
        await session.flush()
        user_id, aid = user.id, account.id
    try:
        yield aid
    finally:
        async with session_scope() as session:
            await session.execute(delete(User).where(User.id == user_id))


async def _account(aid: uuid.UUID) -> Account:
    async with session_scope() as session:
        account = await session.get(Account, aid)
        assert account is not None
        return account


def test_what_counts_as_temporary() -> None:
    assert is_temporary(ProviderConnectError("cannot connect"))
    assert is_temporary(TimeoutError())
    assert is_temporary(ConnectionResetError())
    assert is_temporary(aioimaplib.CommandTimeout("uid move"))
    # After the connection drops, aioimaplib refuses commands this way.
    assert is_temporary(aioimaplib.Abort("command UID illegal in state LOGOUT"))
    assert not is_temporary(aioimaplib.Abort("server has not MOVE capability"))
    assert not is_temporary(ProviderAuthError("bad password"))
    assert not is_temporary(ProviderRejectedError("550 no such user"))
    assert not is_temporary(ValueError("bug"))


def test_smtp_errors_say_whether_to_retry() -> None:
    assert isinstance(_smtp_error(aiosmtplib.SMTPConnectError("refused")), ProviderConnectError)
    assert isinstance(_smtp_error(aiosmtplib.SMTPServerDisconnected("gone")), ProviderConnectError)
    assert isinstance(
        _smtp_error(aiosmtplib.SMTPResponseException(451, "try later")), ProviderConnectError
    )
    assert isinstance(
        _smtp_error(aiosmtplib.SMTPResponseException(554, "rejected")), ProviderRejectedError
    )
    assert isinstance(
        _smtp_error(aiosmtplib.SMTPAuthenticationError(535, "bad credentials")), ProviderAuthError
    )
    refused = aiosmtplib.SMTPRecipientsRefused(
        [aiosmtplib.SMTPRecipientRefused(550, "no such user", "x@example.com")]
    )
    assert isinstance(_smtp_error(refused), ProviderRejectedError)
    greylisted = aiosmtplib.SMTPRecipientsRefused(
        [aiosmtplib.SMTPRecipientRefused(450, "greylisted", "x@example.com")]
    )
    assert isinstance(_smtp_error(greylisted), ProviderConnectError)


async def test_unreachable_after_failures_in_a_row_then_clears(account_id: uuid.UUID) -> None:
    health = AccountHealth(account_id)
    for _ in range(UNREACHABLE_AFTER - 1):
        await health.failed(ProviderConnectError("cannot connect"))
    assert (await _account(account_id)).sync_error is None  # a blip is not an outage

    await health.failed(ProviderConnectError("cannot connect"))
    account = await _account(account_id)
    assert account.sync_error == "unreachable" and account.sync_error_since is not None
    assert account.state == "live"  # still synced: retried until it answers

    await health.ok()
    account = await _account(account_id)
    assert account.sync_error is None and account.sync_error_since is None


async def test_mark_survives_a_restart_and_clears_on_success(account_id: uuid.UUID) -> None:
    first = AccountHealth(account_id)
    for _ in range(UNREACHABLE_AFTER):
        await first.failed(ProviderConnectError("cannot connect"))
    # A new worker knows nothing of the mark, yet its first success clears it.
    await AccountHealth(account_id).ok()
    assert (await _account(account_id)).sync_error is None


async def test_refused_sign_in_stops_syncing(account_id: uuid.UUID) -> None:
    health = AccountHealth(account_id)
    for _ in range(AUTH_GIVE_UP_AFTER - 1):
        await health.failed(ProviderAuthError("AUTHENTICATIONFAILED"))
    assert (await _account(account_id)).state == "live"

    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