Can't send emails with SMTP - Getting Authentication Failed

[EmilianoEscobedo]

Describe the bug
Can't send emails with SMTP using zoho as mail provider, with Authentik deployed in docker-compose. I'm using SSL port 465. Getting Authentication Failed.

To Reproduce

1. Use the environment variables to configure SMTP as documentation says.
2. Complete those environment variables in .env file.
3. Try to send a mail with ak test_mail, executing docker compose exec authentik-worker ak test_email <my_mail>

Expected behavior
Test mail sent.

Screenshots

Logs

Version and Deployment (please complete the following information):

• authentik version: 2024.6.0
• Deployment: docker-compose

Additional context

This instance of Authentik is hosted in a VM of a cloud provider and its restricted in port 80/443 to be only accessible thru a VPN.

Tried from an external online SMTP tester and is working as expected with the exact same server, port, and credentials.

[EmilianoEscobedo]

Hey all, I just downgraded to 2024.4.0 and everything is working as expected, so this seems to be a bug in this last release.

[flece]

same Version and deploymentmethod for me and i got this errormessage for testing E-Mail

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 739, in login
(code, resp) = self.auth(
^^^^^^^^^^
File "/usr/local/lib/python3.12/smtplib.py", line 641, in auth
response = encode_base64(initial_response.encode('ascii'), eol='')
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
builtins.UnicodeEncodeError: 'ascii' codec can't encode characters in position 21-22: ordinal not in range(128)"

[BeryJu]

@flece could it be that in your .env file, the password entry has an invisible unicode character in it?

could both of you run dump_config to ensure authentik reads the .env file correctly? https://docs.goauthentik.io/docs/installation/configuration#verify-your-configuration-settings

[flece]

@BeryJu

i have the characters "ü" and "ß" in my password
if i dump the config it is represented as: "\u00fc" and "\u00df"

if i change to a password without this characters it worked.

[authentik-automation]

This issue has been automatically marked as stale because it has not had recent activity. It will be closed if no further activity occurs. Thank you for your contributions.

[nicoduck]

Hi,

anything new? Complex passwords cause issues with some characters, is there another way to save them to config without the scripts breaking?