Crowd Send test email fails with smtpsendfailedexception 530 5.7.1 client was not authenticated

[P]

Im working with Crowd version 3.5.1 and currently no user is able to receive an email from the application.

When I try to send a test email, I receive the following error:

smtpsendfailedexception 530 5.7.1 client was not authenticated

following this documentation:

https://confluence.atlassian.com/jirakb/cannot-send-test-mail-due-to-authentication-error-300814744.html

Im able to telnet to my mail server without a password over port 465, but for some reason I cant send a test email over the same port both while inputting a username/password combination or just by leaving that part blank.

Has anyone else experienced this situation before?