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

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?

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