This might be a tough thing to figure out but i have to give it a try.

With no changes i am aware of, my jenkins just stopped sending out e-mail 
notifications. I use jenkins 1.609 and email extension plugin 2.40.5. 
Jenkins runs as a service using a service-user who also has the rights on 
the server to send e-mails. Ports to our smtp-server are unlocked. Used 
telnet for testing that everything works as expected. SMTP-server works 
fine, so it has something to do with jenkins and i cant figure out what is 
going wrong.  When i use the test-feature that jenkins offers i get: 
javax.mail.AuthenticationFailedException: 
535 5.7.3 Authentication unsuccessful which tells me that either user or pw 
is incorrect, but i've checked many times, it's setup correctly. Can anyone 
help out with this?
  
After decrypting the password i can safely say that jenkins does save the 
password correct. 

 

Pw is set to not expire, because of reasons like this. Checked anyway, but 
its working as intended.

I also installed the Powershell-Plugin to test if Jenkins would send a mail 
using the script.  I created a job that sends a mail using the powershell 
script and another mail right after using the mailer plugin. Script works 
fine, mailer plugin fails.

I asked the same question on Stack Overflow, it did not solve my problem 
sadly.

Any help is greatly appreciated!

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