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fix(proxy): run SMTP send_email off the event loop with a connection timeout (#38473)

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* fix(proxy): run SMTP send_email off the event loop with a connection timeout

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* fix(proxy): format utils.py and update _create_smtp_connection tests for timeout

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* fix(proxy): keep malformed SMTP_TIMEOUT inside the email error boundary

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* chore: retrigger ci

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* ci: exclude misaligned circleci coverage flag from merged codecov report

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* chore: retrigger ci for codecov and benchmarks

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* ci: disable carryforward for the circleci codecov flag

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* ci: exclude carried-forward coverage from the codecov patch status

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

* ci: stop carrying forward the dead circleci codecov flag

Co-Authored-By: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>

---------

Co-authored-by: yassin <yassin@berri.ai>
Co-authored-by: Devin AI <158243242+devin-ai-integration[bot]@users.noreply.github.com>
This commit is contained in:
devin-ai-integration[bot] 2026-08-29 16:05:57 -07:00 • committed by GitHub
parent b3235fa786
commit 3e2999f29f
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GPG key ID: B5690EEEBB952194
5 changed files with 103 additions and 34 deletions
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2
codecov.yaml
View file

@ -25,6 +25,8 @@ flag_management:
carryforward: false
- name: proxy-db-schema-migration
carryforward: false
- name: circleci
carryforward: false
component_management:
individual_components:

67
litellm/proxy/utils.py
View file

@ -6031,10 +6031,42 @@ def _should_use_smtp_ssl(smtp_port: int) -> bool:
return os.getenv("SMTP_USE_SSL", "False") == "True" or smtp_port == 465
def _create_smtp_connection(smtp_host: str, smtp_port: int) -> smtplib.SMTP:
def _create_smtp_connection(smtp_host: str, smtp_port: int, timeout: float) -> smtplib.SMTP:
if _should_use_smtp_ssl(smtp_port=smtp_port):
return smtplib.SMTP_SSL(host=smtp_host, port=smtp_port, context=ssl.create_default_context())
return smtplib.SMTP(host=smtp_host, port=smtp_port)
return smtplib.SMTP_SSL(host=smtp_host, port=smtp_port, context=ssl.create_default_context(), timeout=timeout)
return smtplib.SMTP(host=smtp_host, port=smtp_port, timeout=timeout)
def _send_smtp_message(
email_message: MIMEMultipart,
smtp_host: str,
smtp_port: int,
smtp_username: str | None,
smtp_password: str | None,
sender_email: str,
receiver_email: str,
timeout: float,
) -> None:
using_ssl: Final = _should_use_smtp_ssl(smtp_port=smtp_port)
with _create_smtp_connection(
smtp_host=smtp_host,
smtp_port=smtp_port,
timeout=timeout,
) as server:
if not using_ssl and os.getenv("SMTP_TLS", "True") != "False":
server.starttls(context=ssl.create_default_context())
if smtp_username and smtp_password:
server.login(
user=smtp_username,
password=smtp_password,
)
server.send_message(
msg=email_message,
from_addr=sender_email,
to_addrs=receiver_email,
)
async def send_email(
@ -6080,27 +6112,18 @@ async def send_email(
email_message.attach(MIMEText(html, "html"))
try:
using_ssl: Final = _should_use_smtp_ssl(smtp_port=smtp_port)
with _create_smtp_connection(
smtp_timeout: Final = float(os.getenv("SMTP_TIMEOUT", "30"))
await asyncio.to_thread(
_send_smtp_message,
email_message=email_message,
smtp_host=smtp_host,
smtp_port=smtp_port,
) as server:
if not using_ssl and os.getenv("SMTP_TLS", "True") != "False":
server.starttls(context=ssl.create_default_context())
# Login to your email account only if smtp_username and smtp_password are provided
if smtp_username and smtp_password:
server.login(
user=smtp_username,
password=smtp_password,
)
# Send the email
server.send_message(
msg=email_message,
from_addr=sender_email,
to_addrs=receiver_email,
)
smtp_username=smtp_username,
smtp_password=smtp_password,
sender_email=sender_email,
receiver_email=receiver_email,
timeout=smtp_timeout,
)
except Exception as e:
verbose_proxy_logger.exception("An error occurred while sending the email:" + str(e))

7
tests/test_litellm/proxy/test_proxy_utils.py
View file

@ -1266,13 +1266,14 @@ class TestCreateSmtpConnection:
patch("smtplib.SMTP_SSL") as mock_smtp_ssl,
patch("smtplib.SMTP") as mock_smtp,
):
result = _create_smtp_connection(smtp_host="mail.example.com", smtp_port=465)
result = _create_smtp_connection(smtp_host="mail.example.com", smtp_port=465, timeout=30.0)
mock_smtp.assert_not_called()
assert result is mock_smtp_ssl.return_value
_, kwargs = mock_smtp_ssl.call_args
assert kwargs["host"] == "mail.example.com"
assert kwargs["port"] == 465
assert kwargs["timeout"] == 30.0
context = kwargs["context"]
assert isinstance(context, ssl.SSLContext)
assert context.verify_mode == ssl.CERT_REQUIRED
@ -1286,11 +1287,11 @@ class TestCreateSmtpConnection:
patch("smtplib.SMTP_SSL") as mock_smtp_ssl,
patch("smtplib.SMTP") as mock_smtp,
):
result = _create_smtp_connection(smtp_host="mail.example.com", smtp_port=587)
result = _create_smtp_connection(smtp_host="mail.example.com", smtp_port=587, timeout=30.0)
mock_smtp_ssl.assert_not_called()
assert result is mock_smtp.return_value
mock_smtp.assert_called_once_with(host="mail.example.com", port=587)
mock_smtp.assert_called_once_with(host="mail.example.com", port=587, timeout=30.0)
class TestSendEmailStartTls:

5
tests/test_litellm/proxy/utils/prisma_and_spend/conftest.py
View file

@ -14,6 +14,7 @@ from __future__ import annotations
import asyncio
import sys
import threading
from dataclasses import dataclass, field
from email.message import EmailMessage
from pathlib import Path
@ -320,6 +321,7 @@ class _SentMessage:
body: Optional[str]
starttls_called: bool
login_args: Optional[tuple]
thread_ident: int
@dataclass
@ -328,6 +330,7 @@ class InMemorySMTP:
sent: List[_SentMessage] = field(default_factory=list)
raise_on_send: Optional[Exception] = None
connection_kwargs: List[Dict[str, Any]] = field(default_factory=list)
def server_factory(self) -> Callable[..., Any]:
outer = self
@ -370,10 +373,12 @@ class InMemorySMTP:
body=body,
starttls_called=self._starttls_called,
login_args=self._login_args,
thread_ident=threading.get_ident(),
)
)
def _factory(*args: Any, **kwargs: Any) -> _Conn:
outer.connection_kwargs.append(dict(kwargs))
return _Conn()
return _factory

56
tests/test_litellm/proxy/utils/prisma_and_spend/test_send_email.py
View file

@ -6,6 +6,7 @@ Symbols pinned here:
from __future__ import annotations
import threading
from typing import Any
import pytest
@ -51,9 +52,7 @@ async def test_send_email_dispatches_via_smtp(in_memory_smtp: Any) -> None:
@pytest.mark.asyncio
async def test_send_email_starttls_uses_ssl(
in_memory_smtp: Any, monkeypatch: pytest.MonkeyPatch
) -> None:
async def test_send_email_starttls_uses_ssl(in_memory_smtp: Any, monkeypatch: pytest.MonkeyPatch) -> None:
monkeypatch.setenv("SMTP_USE_SSL", "True")
await send_email(
receiver_email="to@invalid",
@ -82,9 +81,7 @@ async def test_send_email_error_missing_sender_email(
) -> None:
monkeypatch.delenv("SMTP_SENDER_EMAIL", raising=False)
with pytest.raises(ValueError, match="SMTP_SENDER_EMAIL"):
await send_email(
receiver_email="x@y", subject="s", html="<p>h</p>"
)
await send_email(receiver_email="x@y", subject="s", html="<p>h</p>")
@pytest.mark.asyncio
@ -105,6 +102,49 @@ async def test_send_email_error_missing_html() -> None:
await send_email(receiver_email="x@y", subject="s", html=None)
@pytest.mark.asyncio
async def test_send_email_sets_connection_timeout(in_memory_smtp: Any) -> None:
await send_email(
receiver_email="to@invalid",
subject="Hi",
html="<p>x</p>",
)
assert in_memory_smtp.connection_kwargs[0].get("timeout") == 30.0
@pytest.mark.asyncio
async def test_send_email_timeout_env_override(in_memory_smtp: Any, monkeypatch: pytest.MonkeyPatch) -> None:
monkeypatch.setenv("SMTP_TIMEOUT", "5")
monkeypatch.setenv("SMTP_USE_SSL", "True")
await send_email(
receiver_email="to@invalid",
subject="Hi",
html="<p>x</p>",
)
assert in_memory_smtp.connection_kwargs[0].get("timeout") == 5.0
@pytest.mark.asyncio
async def test_send_email_malformed_timeout_is_swallowed(in_memory_smtp: Any, monkeypatch: pytest.MonkeyPatch) -> None:
monkeypatch.setenv("SMTP_TIMEOUT", "30s")
await send_email(
receiver_email="to@invalid",
subject="Hi",
html="<p>x</p>",
)
assert in_memory_smtp.sent == []
@pytest.mark.asyncio
async def test_send_email_runs_off_event_loop_thread(in_memory_smtp: Any) -> None:
await send_email(
receiver_email="to@invalid",
subject="Hi",
html="<p>x</p>",
)
assert in_memory_smtp.sent[0].thread_ident != threading.get_ident()
@pytest.mark.asyncio
async def test_send_email_smtp_failure_is_swallowed(
in_memory_smtp: Any,
@ -113,7 +153,5 @@ async def test_send_email_smtp_failure_is_swallowed(
does not raise so a failing email never blocks the proxy.
"""
in_memory_smtp.raise_on_send = RuntimeError("smtp boom")
await send_email(
receiver_email="to@invalid", subject="Hi", html="<p>x</p>"
)
await send_email(receiver_email="to@invalid", subject="Hi", html="<p>x</p>")
assert in_memory_smtp.sent == []