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SMTP TLS/SSL not working anymore #2745

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@StefanIGit

Description

@StefanIGit

Environment

self-hosted (https://develop.sentry.dev/self-hosted/)

Steps to Reproduce

upgrade to 24.1.0 from 23.8.0
from sentry/config.yml

mail.backend: 'smtp'
mail.host: mail6.server.tld
mail.password: 'secret'
mail.username: '[email protected]'
mail.from: '[email protected]'
mail.use-ssl: true
mail.port: 587

it worked before
the settings are correct since they work fine with Thunderbird

The server requires "STARTTLS"
it is try
mail.use-ssl: false
or
mail.use-tls: true
or
mail.use-ssl: false
mail.use-tls: false
I get error like
SMTPServerDisconnected('Connection unexpectedly closed: timed out')
and
SMTPNotSupportedError('SMTP AUTH extension not supported by server.')

Expected Result

sending email (invite/pwrest) successfully

Actual Result

errors in log

sentry-self-hosted-worker-1                                        | 10:15:48 [ERROR] celery.app.trace: Task sentry.tasks.email.send_email[6b605357-fb39-4788-a43d-8e68b58d49cf] raised unexpected: SSLError(1, '[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1007)') (data={'hostname': 'celery@a75b7517a419', 'id': '6b605357-fb39-4788-a43d-8e68b58d49cf', 'name': 'sentry.tasks.email.send_email', 'exc': "SSLError(1, '[SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1007)')", 'traceback': 'Traceback (most recent call last):\n  File "/usr/local/lib/python3.10/site-packages/celery/app/trace.py", line 477, in trace_task\n    R = retval = fun(*args, **kwargs)\n  File "/usr/local/lib/python3.10/site-packages/sentry_sdk/integrations/celery.py", line 306, in _inner\n    reraise(*exc_info)\n  File "/usr/local/lib/python3.10/site-packages/sentry_sdk/_compat.py", line 115, in reraise\n    raise value\n  File "/usr/local/lib/python3.10/site-packages/sentry_sdk/integrations/celery.py", line 301, in _inner\n    return f(*args, **kwargs)\n  File "/usr/local/lib/python3.10/site-packages/celery/app/trace.py", line 760, in __protected_call__\n    return self.run(*args, **kwargs)\n  File "/usr/local/lib/python3.10/site-packages/sentry/silo/base.py", line 145, in override\n    return original_method(*args, **kwargs)\n  File "/usr/local/lib/python3.10/site-packages/sentry/tasks/base.py", line 117, in _wrapped\n    result = func(*args, **kwargs)\n  File "/usr/local/lib/python3.10/site-packages/sentry/tasks/email.py", line 55, in send_email\n    send_messages([message])\n  File "/usr/local/lib/python3.10/site-packages/sentry/utils/email/send.py", line 17, in send_messages\n    sent = connection.send_messages(messages)\n  File "/usr/local/lib/python3.10/site-packages/django/core/mail/backends/smtp.py", line 102, in send_messages\n    new_conn_created = self.open()\n  File "/usr/local/lib/python3.10/site-packages/django/core/mail/backends/smtp.py", line 62, in open\n    self.connection = self.connection_class(self.host, self.port, **connection_params)\n  File "/usr/local/lib/python3.10/smtplib.py", line 1050, in __init__\n    SMTP.__init__(self, host, port, local_hostname, timeout,\n  File "/usr/local/lib/python3.10/smtplib.py", line 255, in __init__\n    (code, msg) = self.connect(host, port)\n  File "/usr/local/lib/python3.10/smtplib.py", line 341, in connect\n    self.sock = self._get_socket(host, port, self.timeout)\n  File "/usr/local/lib/python3.10/smtplib.py", line 1057, in _get_socket\n    new_socket = self.context.wrap_socket(new_socket,\n  File "/usr/local/lib/python3.10/ssl.py", line 513, in wrap_socket\n    return self.sslsocket_class._create(\n  File "/usr/local/lib/python3.10/ssl.py", line 1104, in _create\n    self.do_handshake()\n  File "/usr/local/lib/python3.10/ssl.py", line 1375, in do_handshake\n    self._sslobj.do_handshake()\nssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1007)\n', 'args': '()', 'kwargs': "{'message': <django.core.mail.message.EmailMultiAlternatives object at 0x7fe621961990>, '__start_time': 1706523347.505079}", 'description': 'raised unexpected', 'internal': False})

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24.1.0

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