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Bug
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Resolution: Incomplete
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Major
I used the email-ext to set up notifications for build success, but had Jenkins set up to use an smtp server that was company-internal. This worked fine when I only had company internal mail recipients, but when I added an outside recipient, the build failed because email-ext returned an SMTPException: Could not deliver. All this is fine and expected in a PEBKAC situation.
However, when I had set up a new, proper smtp server in Jenkins and sent successful test emails through the Jenkins configuration page, I figured everything would be fine. But the next time a build finished, no emails were sent out even though the build finished as normal. Checking the logs I found that it said:
"
Email was triggered for: Success
Sending email for trigger: Success
"
The two usual last lines with "Sending email to: blah@blah, Finished: SUCCESS" were missing. Obviously email-ext was unable to recover from the previous error even though the settings had been corrected. I worked around the problem by restarting Jenkins, and everything started working as expected with the new configuration.
[JENKINS-15311] Email-ext can't recover after a failed smtp delivery
If the "Sending email to:..." is not logged, then no email is being sent, so there is no false positive.
Please try using the override default settings feature of email-ext and see if you see the same issue. I want to isolate if something changed in core (which is used if you don't override).
The current behavior is "Sending email for trigger: Success" and then nothing. It'd be better to have a line that says "Unable to send email. Email-ext can't recover from errors. Please restart Jenkins and try again."
I restarted Jenkins so I can no longer reproduce the error. I didn't override default settings though.
bootstraponline
added a comment - - edited The current behavior is "Sending email for trigger: Success" and then nothing. It'd be better to have a line that says "Unable to send email. Email-ext can't recover from errors. Please restart Jenkins and try again."
I restarted Jenkins so I can no longer reproduce the error. I didn't override default settings though. If the core emailer never returns, then I can't log something saying there was an error. It's a closed box basically.
I have no way of replicating this, so it will only get some traction if someone is willing to run with a debug version of the plugin.
bootstraponline
added a comment - I'll try to reproduce the issue on a local Jenkins install. Where is the debug version of the plugin?
bootstraponline
added a comment - I'll try to reproduce the issue on a local Jenkins install. Where is the debug version of the plugin? 
Couldn't the success detection logic be improved to determine if an email was truly sent or not? The issue isn't so much that email-ext doesn't recover after failure, rather it's the false positive of claiming success when no email has been sent.