smtplib.SMTPNotSupportedError: SMTP AUTH extension not supported by server. When attempting to connect from and authentik server

[SpaceFlier]

Im running PMG and iRedMail as my mail gateway/service and have gotten everything setup correclty. My immich instance is able to connect and send emails to my gmail account using the following configuration:

when I run an email test from the authentik server using the

docker compose exec worker ak test_email mx.*********.***

command i get the following:

Traceback (most recent call last):
  File "<frozen runpy>", line 198, in _run_module_as_main
  File "<frozen runpy>", line 88, in _run_code
  File "/manage.py", line 52, in <module>
    execute_from_command_line(sys.argv)
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/management/__init__.py", line 442, in execute_from_command_line
    utility.execute()
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/management/__init__.py", line 436, in execute
    self.fetch_command(subcommand).run_from_argv(self.argv)
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/management/base.py", line 413, in run_from_argv
    self.execute(*args, **cmd_options)
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/management/base.py", line 459, in execute
    output = self.handle(*args, **options)
             ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/authentik/tenants/management/__init__.py", line 38, in handle
    self.handle_per_tenant(*args, **options)
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/management/base.py", line 107, in wrapper
    res = handle_func(*args, **kwargs)
          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/authentik/stages/email/management/commands/test_email.py", line 38, in handle_per_tenant
    send_mail(message.__dict__, stage.pk)
  File "/ak-root/venv/lib/python3.12/site-packages/celery/local.py", line 182, in __call__
    return self._get_current_object()(*a, **kw)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/ak-root/venv/lib/python3.12/site-packages/celery/app/task.py", line 411, in __call__
    return self.run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/ak-root/venv/lib/python3.12/site-packages/celery/app/autoretry.py", line 60, in run
    ret = task.retry(exc=exc, **retry_kwargs)
          ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/ak-root/venv/lib/python3.12/site-packages/celery/app/task.py", line 720, in retry
    raise_with_context(exc or Retry('Task can be retried', None))
  File "/ak-root/venv/lib/python3.12/site-packages/celery/app/autoretry.py", line 38, in run
    return task._orig_run(*args, **kwargs)
           ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
  File "/authentik/stages/email/tasks.py", line 105, in send_mail
    raise exc
  File "/authentik/stages/email/tasks.py", line 73, in send_mail
    backend.open()
  File "/ak-root/venv/lib/python3.12/site-packages/django/core/mail/backends/smtp.py", line 95, in open
    self.connection.login(self.username, self.password)
  File "/usr/local/lib/python3.12/smtplib.py", line 716, in login
    raise SMTPNotSupportedError(
smtplib.SMTPNotSupportedError: SMTP AUTH extension not supported by server.
Sentry is attempting to send 1 pending events
Waiting up to 2 seconds
Press Ctrl-C to quit

My .env file for authentik relating to smtp has the same settings as the immich instance:

# SMTP Host Emails are sent to
AUTHENTIK_EMAIL__HOST=mx.*******.***
AUTHENTIK_EMAIL__PORT=587
# Optionally authenticate (don't add quotation marks to your password)
AUTHENTIK_EMAIL__USERNAME=authentik@**********.***
AUTHENTIK_EMAIL__PASSWORD=**************
# Use StartTLS
AUTHENTIK_EMAIL__USE_TLS=true
# Use SSL
AUTHENTIK_EMAIL__USE_SSL=false
AUTHENTIK_EMAIL__TIMEOUT=10
# Email address authentik will send from, should have a correct @domain
AUTHENTIK_EMAIL__FROM=authentik@***********.***

I'm not sure whats causing authentik to fail and immich to work fine, and from what i can see with that error its mainly people writing their own python scripts and implementing an smtp server and missing a line or something like that.
Sorry if im missing something important, ive been trying to get this to work for the past 4 hours and im almost burnt out (thus posting on the forums hoping ill get a miracle)

 

[Stoiko Ivanov]

smtplib.SMTPNotSupportedError: SMTP AUTH extension not supported by server.

This error message indicates that the software wants to authenticate with SMTP AUTH - PMG does not have a user-database or authentication on SMTP level (as it's meant to be deployed between the internet and your internal mail-server (which is usually the point where you authenticate)):
https://pmg.proxmox.com/pmg-docs/pmg-admin-guide.html#chapter_deployment

I hope this helps!

 

[SpaceFlier]

Ahh thanks this seems to be what I was missing. I'll try disabling authentication on authentik and see if that fixes it