SSL: WRONG_VERSION_NUMBER

[Shablone]

I added smtp configuration via environment variables to my docker-compose setup.
I use gmail app passwords for that.

At first I tried this config:

EMAIL_HOST="smtp.gmail.com"
EMAIL_PORT=587
EMAIL_USE_TLS=True
EMAIL_HOST_USER="xxxx"
EMAIL_HOST_PASSWORD="xxx"

Then I changed the port to 465 and restarted the compose.
Both setups throw an error in celery when a new user tries to register:

Task gramps_webapi.api.tasks.send_email_confirm_email[5d7d0d60-daa9-4961-9dd7-98d8bb59eca5] raised unexpected: ValueError('Error while trying to send e-mail.')
grampsweb_celery  | Traceback (most recent call last):
grampsweb_celery  |   File "/usr/local/lib/python3.11/dist-packages/gramps_webapi/api/util.py", line 399, in send_email
grampsweb_celery  |     smtp = smtplib.SMTP_SSL(host=host, port=port, timeout=10)
grampsweb_celery  |            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/lib/python3.11/smtplib.py", line 1050, in __init__
grampsweb_celery  |     SMTP.__init__(self, host, port, local_hostname, timeout,
grampsweb_celery  |   File "/usr/lib/python3.11/smtplib.py", line 255, in __init__
grampsweb_celery  |     (code, msg) = self.connect(host, port)
grampsweb_celery  |                   ^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/lib/python3.11/smtplib.py", line 341, in connect
grampsweb_celery  |     self.sock = self._get_socket(host, port, self.timeout)
grampsweb_celery  |                 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/lib/python3.11/smtplib.py", line 1057, in _get_socket
grampsweb_celery  |     new_socket = self.context.wrap_socket(new_socket,
grampsweb_celery  |                  ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/lib/python3.11/ssl.py", line 517, in wrap_socket
grampsweb_celery  |     return self.sslsocket_class._create(
grampsweb_celery  |            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/lib/python3.11/ssl.py", line 1075, in _create
grampsweb_celery  |     self.do_handshake()
grampsweb_celery  |   File "/usr/lib/python3.11/ssl.py", line 1346, in do_handshake
grampsweb_celery  |     self._sslobj.do_handshake()
grampsweb_celery  | ssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:992)
grampsweb_celery  |
grampsweb_celery  |
grampsweb_celery  | During handling of the above exception, another exception occurred:
grampsweb_celery  |
grampsweb_celery  |
grampsweb_celery  | Traceback (most recent call last):
grampsweb_celery  |   File "/usr/local/lib/python3.11/dist-packages/celery/app/trace.py", line 477, in trace_task
grampsweb_celery  |     R = retval = fun(*args, **kwargs)
grampsweb_celery  |                  ^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/local/lib/python3.11/dist-packages/gramps_webapi/util/celery.py", line 20, in __call__
grampsweb_celery  |     return self.run(*args, **kwargs)
grampsweb_celery  |            ^^^^^^^^^^^^^^^^^^^^^^^^^
grampsweb_celery  |   File "/usr/local/lib/python3.11/dist-packages/gramps_webapi/api/tasks.py", line 77, in send_email_confirm_email
grampsweb_celery  |     send_email(subject=subject, body=body, to=[email])
grampsweb_celery  |   File "/usr/local/lib/python3.11/dist-packages/gramps_webapi/api/util.py", line 418, in send_email
grampsweb_celery  |     raise ValueError("Error while trying to send e-mail.")
grampsweb_celery  | ValueError: Error while trying to send e-mail.

[DavidMStraub]

Please don't open an issue for configuration problems.

[Shablone]

Well I think its a problem of the app and not the configuration

[askurashev]

Hi. Have you solved problem with SSL: WRONG_VERSION_NUMBER? I got the same error.

[Shablone]

Well, that was quite a while ago.
I think I got it working by switching and double checking ports and protocols (ssl, starttls), while also making sure that the configuration really got applied and not being ignored in favor of the initial not working configuration