I'm trying to setup the email notification in Jenkins to create an alert when a build has failed.

I am using Jenkins 2.204.2 and mailer plugin 1.30

I have tried with AWS and Gmail authentication. I encounter exactly the same problem on both.

In both cases after I've entered all of my SMTP server details I am able to successfully send a test email. I receive the test email externally as well.

If I click apply and then test configuration I still get "Email was successfully sent"

However when I click "Save" and then go back to "Manage Jenkins" -> "Configure System" and "Test configuration by sending test e-mail" when I send a test email I get the following error:

"Failed to send out e-mail javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8  https://support.google.com/mail/?p=BadCredentials r8sm514463pjo.22 - gsmtp"

or "Failed to send out e-mail

javax.mail.AuthenticationFailedException: 535 Authentication Credentials Invalid

at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:809)
at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:752)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:669)"

Additionally what concerns me is whenever I go to the configure page of jenkins it shows the notepad with a pen icon indicating that "One or more fields in this block have been edited". But that is without any edits having been made from my side?

I've managed to get it working using gmail's SMTP, but in order to get it working I have to "save" the password when I receive a chrome "would you like to update your password" popup. This password popup should be in relation to my login details for the site, and not for the SMTP login details which I have already "saved" on the page.

The same process does not work for AWS. It might be because the AWS details that I'm using has a "/" in the password.