Getting AuthenticationFailedException: 535 5.7.3 error when trying to set up SMTP mail server.

[Michael Winn]

When I am trying to set up an outgoing SMTP mail server, with basic authentication, I get the following error, "AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful" Nothing further follows. What could be causing this issue? My Jira server is set up on a private network without internet access. It is set to port 25, the authentication method is Password "(basic authentication)"

[Benjamin]

HI @Michael Winn ,

Looks like you have the same issue as this post below. You may need to look into your server settings or create a connector.

https://community.atlassian.com/t5/Jira-questions/Outgoing-SMTP-Mail-Server-Authentication-Unsuccessful/qaq-p/1434010