#34524: Error while sending TLS smtp email on "self-signed certificate" server
---------------------------------------+------------------------
               Reporter:  Buky         |          Owner:  nobody
                   Type:  Bug          |         Status:  new
              Component:  Core (Mail)  |        Version:  4.2
               Severity:  Normal       |       Keywords:  ssl
           Triage Stage:  Unreviewed   |      Has patch:  0
    Needs documentation:  0            |    Needs tests:  0
Patch needs improvement:  0            |  Easy pickings:  0
                  UI/UX:  0            |
---------------------------------------+------------------------
 The issue appears in Django 4.2 (tested with Python 3.11 and Python 3.9).
 Correctly works with previous versions of Django: 3.2 and 4.1

 Context: I use locally use the [https://proton.me/support/protonmail-
 bridge-install protonmail-bridge] solution that locally bind an `IMAP` and
 `SMTP` ports with `STARTTLS`. Then, I use in my project config the
 [https://docs.djangoproject.com/en/4.2/topics/email/#smtp-backend
 EmailBackend] to connect to the solution and send emails.

 Here is the traceback, when I try to send emails with Django 4.2:
 {{{
 Traceback (most recent call last):
   File "/home/user/my-project/manage.py", line 15, in <module>
     execute_from_command_line(sys.argv)
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/management/__init__.py", line 442, in
 execute_from_command_line
     utility.execute()
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/management/__init__.py", line 436, in execute
     self.fetch_command(subcommand).run_from_argv(self.argv)
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/management/base.py", line 412, in run_from_argv
     self.execute(*args, **cmd_options)
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/management/base.py", line 458, in execute
     output = self.handle(*args, **options)
              ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
   File "/home/user/my-project/my-app/management/commands/send-mail.py",
 line 62, in handle
     send_mail(f"[My subject] {options['subject']}",
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/mail/__init__.py", line 87, in send_mail
     return mail.send()
            ^^^^^^^^^^^
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/mail/message.py", line 298, in send
     return self.get_connection(fail_silently).send_messages([self])
            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/mail/backends/smtp.py", line 127, in send_messages
     new_conn_created = self.open()
                        ^^^^^^^^^^^
   File "/home/user/.virtualenvs/env/lib/python3.11/site-
 packages/django/core/mail/backends/smtp.py", line 92, in open
     self.connection.starttls(context=self.ssl_context)
   File "/usr/lib/python3.11/smtplib.py", line 790, in starttls
     self.sock = context.wrap_socket(self.sock,
                 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
   File "/usr/lib/python3.11/ssl.py", line 517, in wrap_socket
     return self.sslsocket_class._create(
            ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
   File "/usr/lib/python3.11/ssl.py", line 1075, in _create
     self.do_handshake()
   File "/usr/lib/python3.11/ssl.py", line 1346, in do_handshake
     self._sslobj.do_handshake()
 ssl.SSLCertVerificationError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate
 verify failed: self-signed certificate (_ssl.c:992)
 }}}

 I found [https://code.djangoproject.com/ticket/34386 another ticket]
 recently created ticket related to SSL issue, but the issue doesn't
 exactly the same and the issue doesn't precisely mention when the patch
 will be merged: `[4.2.x] Fixed`.

 I have tried to export the TLS certificate and key of the solution and add
 them in my `settings.py` like:
 {{{
 EMAIL_SSL_CERTFILE="/tmp/cert.pem"
 EMAIL_SSL_KEYFILE="/tmp/key.pem"
 }}}
 And to put them in the trust store of the system:
 {{{
 cp /tmp/cert.pem /usr/local/share/ca-certificates/protonmail-bridge.crt
 cp /tmp/key.pem /etc/ssl/privateprotonmail-bridge.key
 update-ca-certificates
 }}}
 But both fixes tested didn't work.

-- 
Ticket URL: <https://code.djangoproject.com/ticket/34524>
Django <https://code.djangoproject.com/>
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