SMTP TLS/SSL not working anymore #2745

StefanIGit · 2024-01-29T10:47:44Z

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: 'info@server.tld'
mail.from: 'sentry@server.tld'
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})

Product Area

Settings

Link

No response

DSN

No response

Version

24.1.0

The text was updated successfully, but these errors were encountered:

getsantry · 2024-01-29T10:47:48Z

Assigning to @getsentry/support for routing ⏲️

hubertdeng123 · 2024-01-30T23:02:04Z

Is your server using TLS as well? We've also upgraded successfully without encountering this issue, so I don't think this is a general problem.

Leask · 2024-02-16T05:54:03Z

same here:

worker-1                                        | smtplib.SMTPServerDisconnected: Connection unexpectedly closed: timed out

azaslavsky · 2024-02-20T18:55:23Z

There was a breaking change at 23.11.0 that removed a server that was not on the default SMTP path. Is it possible that either of you were using it?

chris-laack · 2024-02-28T07:14:48Z

We have the same problem since version sentry 24.*. However, it is due to a faulty server certificate. This was not noticed before the changeover to Django Mail Vers. 4.2, as the host entries were not checked.
Since the new Django version this is now necessary.

Error:
SSL: CERTIFICATE_VERIFY_FAILED
This is due to the ssl_context.check_hostname field in the django.core.mail.backends.smtp.py file being set to True by default, starting from Django 4.2.

Unfortunately I have not found a way to work around this using skip ssl validation. In our case it only helps that our mail admin issues a valid server certificate.

hubertdeng123 · 2024-02-29T23:51:06Z

@chris-laack Thanks for your input. Does that help @StefanIGit ?

AwiOnline · 2024-03-14T16:16:23Z

I have the same problem on 23.11.2
It worked before upgrade from 23.8.0

yildizozgur · 2024-06-06T13:33:52Z

Hi We have the same issue on 24.5.0.

13:20:36 [ERROR] django.request: Internal Server Error: /api/0/internal/mail/ (status_code=500 request=<WSGIRequest: POST '/api/0/internal/mail/'>)

I can make an SSL handshake on container. Appliction could not complete SSL verification.

azaslavsky · 2024-06-07T23:03:53Z

Is there no other error information? A 500 error alone doesn't give us much to go on, and usually the logs contain more information about the failed SSL exchange.

yildizozgur · 2024-06-10T09:39:31Z

Hi,
This is my settings:

  backend: smtp
  useTls: true
  useSsl: false
  host: my.mailserver.com:
  from: xxxx
  port: 25
  username: xxxx
  existingSecret: xxxx

I can make a success handshake on the pod.

I have no name!@sentry-qa-worker-xxxxx:/$ openssl s_client -starttls smtp -connect my.mailserver.com:25
CONNECTED(00000003)
depth=2 C = XX, O = XXXX, OU = xxxx.com, CN = XXXX Root CA 
verify error:num=19:self-signed certificate in certificate chain
verify return:1
.....
verify return:1
.....
verify return:1
......
verify return:1
---
Certificate chain
 0 s:O = xxxxxx...............
---
No client certificate CA names sent
Peer signing digest: SHA256
Peer signature type: RSA-PSS
Server Temp Key: X25519, 253 bits
---
SSL handshake has read 3756 bytes and written 433 bytes
Verification error: self-signed certificate in certificate chain
---
New, TLSv1.3, Cipher is TLS_AES_256_GCM_SHA384
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
No ALPN negotiated
Early data was not sent
Verify return code: 19 (self-signed certificate in certificate chain)
---
250 HELP

Here is the all worker certificate settings and pod errors:

/$ more /etc/sentry/sentry.conf.py
SENTRY_SDK_CONFIG = {
    'ca_certs': '/etc/pki/ca-trust/custom/ca.crt',
    "release": sentry.__build__,
    "environment": ENVIRONMENT,
    "in_app_include": ["sentry", "sentry_plugins"],
    "debug": True,
    "send_default_pii": True,
    "auto_enabling_integrations": False,
}

$ env | grep BUNDLE
REQUESTS_CA_BUNDLE=/etc/pki/ca-trust/custom/ca.crt

06:30:00 [INFO] sentry.tasks.auto_ongoing_issues: auto_transition_issues_new_to_ongoing started (first_seen_lte=1717396200 first_seen_lte_datetime=datetime.datetime(2024, 6, 3, 6, 30, tzinfo=datetime.timezone.utc))
Traceback (most recent call last):
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task
    R = retval = fun(*args, **kwargs)
                 ^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner
    reraise(*exc_info)
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise
    raise value
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner
    return f(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__
    return self.run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override
    return original_method(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped
    result = func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email
    send_messages([message])
  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages
    sent = connection.send_messages(messages)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages
    new_conn_created = self.open()
                       ^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open
    self.connection.starttls(context=self.ssl_context)
  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls
    self.sock = context.wrap_socket(self.sock,
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)
06:31:21 [ERROR] celery.app.trace: Task sentry.tasks.email.send_email[0c3eedcd-5946-4f52-a156-f4faa50c32f8] raised unexpected: SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)') (data={'hostname': 'celery@sentry-qa-worker-55ddc48d9d-ftlmp', 'id': '0c3eedcd-5946-4f52-a156-f4faa50c32f8', 'name': 'sentry.tasks.email.send_email', 'exc': "SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)')", 'traceback': 'Traceback (most recent call last):\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task\n    R = retval = fun(*args, **kwargs)\n                 ^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner\n    reraise(*exc_info)\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise\n    raise value\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner\n    return f(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__\n    return self.run(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override\n    return original_method(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped\n    result = func(*args, **kwargs)\n             ^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email\n    send_messages([message])\n  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages\n    sent = connection.send_messages(messages)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages\n    new_conn_created = self.open()\n                       ^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open\n    self.connection.starttls(context=self.ssl_context)\n  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls\n    self.sock = context.wrap_socket(self.sock,\n                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket\n    return self.sslsocket_class._create(\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create\n    self.do_handshake()\n  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake\n    self._sslobj.do_handshake()\nssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)\n', 'args': '()', 'kwargs': "{'message': <django.core.mail.message.EmailMultiAlternatives object at 0x7f078855f850>, '__start_time': 1718001080.878142}", 'description': 'raised unexpected', 'internal': False})
Traceback (most recent call last):
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task
    R = retval = fun(*args, **kwargs)
                 ^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner
    reraise(*exc_info)
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise
    raise value
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner
    return f(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__
    return self.run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override
    return original_method(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped
    result = func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email
    send_messages([message])
  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages
    sent = connection.send_messages(messages)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages
    new_conn_created = self.open()
                       ^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open
    self.connection.starttls(context=self.ssl_context)
  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls
    self.sock = context.wrap_socket(self.sock,
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)
06:31:21 [ERROR] celery.app.trace: Task sentry.tasks.email.send_email[dd8c1177-6176-446a-820b-2f68dff3c94f] raised unexpected: SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)') (data={'hostname': 'celery@sentry-qa-worker-55ddc48d9d-ftlmp', 'id': 'dd8c1177-6176-446a-820b-2f68dff3c94f', 'name': 'sentry.tasks.email.send_email', 'exc': "SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)')", 'traceback': 'Traceback (most recent call last):\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task\n    R = retval = fun(*args, **kwargs)\n                 ^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner\n    reraise(*exc_info)\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise\n    raise value\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner\n    return f(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__\n    return self.run(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override\n    return original_method(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped\n    result = func(*args, **kwargs)\n             ^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email\n    send_messages([message])\n  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages\n    sent = connection.send_messages(messages)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages\n    new_conn_created = self.open()\n                       ^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open\n    self.connection.starttls(context=self.ssl_context)\n  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls\n    self.sock = context.wrap_socket(self.sock,\n                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket\n    return self.sslsocket_class._create(\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create\n    self.do_handshake()\n  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake\n    self._sslobj.do_handshake()\nssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)\n', 'args': '()', 'kwargs': "{'message': <django.core.mail.message.EmailMultiAlternatives object at 0x7f07907cb5d0>, '__start_time': 1718001081.443496}", 'description': 'raised unexpected', 'internal': False})
Traceback (most recent call last):
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task
    R = retval = fun(*args, **kwargs)
                 ^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner
    reraise(*exc_info)
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise
    raise value
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner
    return f(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__
    return self.run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override
    return original_method(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped
    result = func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email
    send_messages([message])
  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages
    sent = connection.send_messages(messages)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages
    new_conn_created = self.open()
                       ^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open
    self.connection.starttls(context=self.ssl_context)
  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls
    self.sock = context.wrap_socket(self.sock,
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)
06:31:22 [ERROR] celery.app.trace: Task sentry.tasks.email.send_email[b2c63c9b-8536-49ea-be25-5e99672168fb] raised unexpected: SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)') (data={'hostname': 'celery@sentry-qa-worker-55ddc48d9d-ftlmp', 'id': 'b2c63c9b-8536-49ea-be25-5e99672168fb', 'name': 'sentry.tasks.email.send_email', 'exc': "SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)')", 'traceback': 'Traceback (most recent call last):\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task\n    R = retval = fun(*args, **kwargs)\n                 ^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner\n    reraise(*exc_info)\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise\n    raise value\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner\n    return f(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__\n    return self.run(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override\n    return original_method(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped\n    result = func(*args, **kwargs)\n             ^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email\n    send_messages([message])\n  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages\n    sent = connection.send_messages(messages)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages\n    new_conn_created = self.open()\n                       ^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open\n    self.connection.starttls(context=self.ssl_context)\n  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls\n    self.sock = context.wrap_socket(self.sock,\n                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket\n    return self.sslsocket_class._create(\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create\n    self.do_handshake()\n  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake\n    self._sslobj.do_handshake()\nssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)\n', 'args': '()', 'kwargs': "{'message': <django.core.mail.message.EmailMultiAlternatives object at 0x7f0788594890>, '__start_time': 1718001081.931252}", 'description': 'raised unexpected', 'internal': False})
Traceback (most recent call last):
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task
    R = retval = fun(*args, **kwargs)
                 ^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner
    reraise(*exc_info)
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise
    raise value
  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner
    return f(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__
    return self.run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override
    return original_method(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped
    result = func(*args, **kwargs)
             ^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email
    send_messages([message])
  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages
    sent = connection.send_messages(messages)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages
    new_conn_created = self.open()
                       ^^^^^^^^^^^
  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open
    self.connection.starttls(context=self.ssl_context)
  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls
    self.sock = context.wrap_socket(self.sock,
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)
06:31:22 [ERROR] celery.app.trace: Task sentry.tasks.email.send_email[d07059e3-fb47-4176-b158-db1587eadbd8] raised unexpected: SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)') (data={'hostname': 'celery@sentry-qa-worker-55ddc48d9d-ftlmp', 'id': 'd07059e3-fb47-4176-b158-db1587eadbd8', 'name': 'sentry.tasks.email.send_email', 'exc': "SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)')", 'traceback': 'Traceback (most recent call last):\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 477, in trace_task\n    R = retval = fun(*args, **kwargs)\n                 ^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 346, in _inner\n    reraise(*exc_info)\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/utils.py", line 1640, in reraise\n    raise value\n  File "/usr/local/lib/python3.11/site-packages/sentry_sdk/integrations/celery/__init__.py", line 341, in _inner\n    return f(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/celery/app/trace.py", line 760, in __protected_call__\n    return self.run(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/silo/base.py", line 146, in override\n    return original_method(*args, **kwargs)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/base.py", line 117, in _wrapped\n    result = func(*args, **kwargs)\n             ^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/sentry/tasks/email.py", line 54, in send_email\n    send_messages([message])\n  File "/usr/local/lib/python3.11/site-packages/sentry/utils/email/send.py", line 18, in send_messages\n    sent = connection.send_messages(messages)\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 128, in send_messages\n    new_conn_created = self.open()\n                       ^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/site-packages/django/core/mail/backends/smtp.py", line 93, in open\n    self.connection.starttls(context=self.ssl_context)\n  File "/usr/local/lib/python3.11/smtplib.py", line 790, in starttls\n    self.sock = context.wrap_socket(self.sock,\n                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 517, in wrap_socket\n    return self.sslsocket_class._create(\n           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^\n  File "/usr/local/lib/python3.11/ssl.py", line 1104, in _create\n    self.do_handshake()\n  File "/usr/local/lib/python3.11/ssl.py", line 1382, in do_handshake\n    self._sslobj.do_handshake()\nssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)\n', 'args': '()', 'kwargs': "{'message': <django.core.mail.message.EmailMultiAlternatives object at 0x7f078830e110>, '__start_time': 1718001082.394444}", 'description': 'raised unexpected', 'internal': False})

hubertdeng123 · 2024-06-11T22:08:43Z

@yildizozgur This may be a similar issue, but also not considering you're using sentry-kubernetes, which isn't supported here.

yildizozgur · 2024-06-12T21:07:21Z

Hi @hubertdeng123 , yes We are running on K8s. But the problem is related on Application, it is not related to the environment. In the pod we can do SSL handshake successfully.

marbon87 · 2024-06-14T14:10:52Z

I am having the same problem without using k8s.

hubertdeng123 · 2024-06-14T20:00:44Z

Thanks for reporting, I'm going to backlog this item for now.

otbutz · 2024-07-15T09:48:15Z

[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self-signed certificate in certificate chain (_ssl.c:1006)

I had the same problem after following the guide in https://develop.sentry.dev/self-hosted/custom-ca-roots/. Please make sure that your certificate has the expected format and file extension. See getsentry/develop#1334

yildizozgur · 2024-10-14T14:25:46Z

Hi @otbutz ,
I have already set *.crt file extention. It still get same error.

[ERROR] django.request: Internal Server Error: /api/0/internal/mail/ (status_code=500 request=<WSGIRequest: POST '/api/0/internal/mail/'>)

Could not get any other log on other pods. I think it is possiible at "SSL verfication" step. I coul not find any configuration parameter to set it "skip SSL sertification" to true.

mojitaleghani · 2024-11-02T13:51:44Z

I have the same error without using k8s.. I am running a self-hosted sentry and facing below errors:

02/Nov/2024:13:50:59 +0000] "POST /api/0/internal/mail/ HTTP/1.1" 500 42 "https://sentry.###/manage/status/mail/" "Mozilla/5.0 (X11; Ubuntu; Linux x86_64; rv:131.0) Gecko/20100101 Firefox/131.0"

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SSL/TLS Verification Fails sentry-kubernetes/charts#1300

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SMTP TLS/SSL not working anymore #2745

SMTP TLS/SSL not working anymore #2745

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SMTP TLS/SSL not working anymore #2745

SMTP TLS/SSL not working anymore #2745

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