My SMTP mail server "From address" is set to "TELS Issuetracker <issuetracker@telscenter.org>". When I click Update, JIRA accepts it without reservation.

I click "Send a Test Email" and the log reports that it succeeded. I also receive it at the specified address.

But when a notification takes place that must send an e-mail, it fails with this error:
2004-10-15 17:19:48,894 ERROR [atlassian.mail.queue.MailQueueImpl] com.atlassian.mail.MailException: Sending failed;
nested exception is:
javax.mail.internet.AddressException: Missing '<' in string ``"Turadg Aleahmad (JIRA)" <TELS Issue
tracker <issuetracker@telscenter.org>>'' at position 73

"Send Test Email" should address the e-mail the same way so it actually tests the addressing.

Further, I would request that the address composer does not prepend "First Last (JIRA) <" to a "From address" if it already matches the "[\w ]+ <.@.>" pattern.

If that's too much, at least make the "From address" field validate its contents.