SMTP encryption broken

[dporki]

The problem

The SMTP integration does not seem to support any kind of encryption. I have tried various pairs since my mailserver supports:

587 STARTTLS/TLS 465 SSL 25 STARTTLS/TLS

None of the above worked, however, encryption set to none worked fine but isn't prefered.

What version of Home Assistant Core has the issue?

core-2024.6.2

What was the last working version of Home Assistant Core?

No response

What type of installation are you running?

Home Assistant OS

Integration causing the issue

smtp

Link to integration documentation on our website

https://www.home-assistant.io/integrations/smtp/

Diagnostics information

No response

Example YAML snippet

notify:
  - name: "hassbot"
    platform: smtp
    server: "mail.your-server.de"
    port: 587
    timeout: 15
    sender: "my@mail.com"
    encryption: tls
    username: "my@mail.com"
    password: "censored"
    recipient:
      - "me@mail.com"
    sender_name: "my@mail.com"

Anything in the logs that might be useful for us?

Traceback (most recent call last):
  File "/usr/src/homeassistant/homeassistant/components/notify/legacy.py", line 104, in async_setup_platform
    notify_service = await hass.async_add_executor_job(
                     ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/concurrent/futures/thread.py", line 58, in run
    result = self.fn(*self.args, **self.kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 103, in get_service
    if mail_service.connection_is_valid():
       ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 165, in connection_is_valid
    server = self.connect()
             ^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 155, in connect
    mail.starttls(context=ssl_context)
  File "/usr/local/lib/python3.12/smtplib.py", line 779, in starttls
    self.sock = context.wrap_socket(self.sock,
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/ssl.py", line 455, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/ssl.py", line 1042, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.12/ssl.py", line 1320, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL] unknown error (_ssl.c:1000)

### Additional information

Another error log slightly different.
'''
Traceback (most recent call last):
  File "/usr/src/homeassistant/homeassistant/components/notify/legacy.py", line 104, in async_setup_platform
    notify_service = await hass.async_add_executor_job(
                     ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/concurrent/futures/thread.py", line 58, in run
    result = self.fn(*self.args, **self.kwargs)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 103, in get_service
    if mail_service.connection_is_valid():
       ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 165, in connection_is_valid
    server = self.connect()
             ^^^^^^^^^^^^^^
  File "/usr/src/homeassistant/homeassistant/components/smtp/notify.py", line 144, in connect
    mail = smtplib.SMTP_SSL(
           ^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/smtplib.py", line 1022, in __init__
    SMTP.__init__(self, host, port, local_hostname, timeout,
  File "/usr/local/lib/python3.12/smtplib.py", line 255, in __init__
    (code, msg) = self.connect(host, port)
                  ^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/smtplib.py", line 341, in connect
    self.sock = self._get_socket(host, port, self.timeout)
                ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/smtplib.py", line 1029, in _get_socket
    new_socket = self.context.wrap_socket(new_socket,
                 ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/ssl.py", line 455, in wrap_socket
    return self.sslsocket_class._create(
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/usr/local/lib/python3.12/ssl.py", line 1042, in _create
    self.do_handshake()
  File "/usr/local/lib/python3.12/ssl.py", line 1320, in do_handshake
    self._sslobj.do_handshake()
ssl.SSLError: [SSL: WRONG_VERSION_NUMBER] wrong version number (_ssl.c:1000)
''''

[home-assistant[bot]]

smtp documentation smtp source