I have installed JIRA on a Windows 2008 R2 server and am in evaluation mode. I was able to configure the outgoing email server and can successfully send a test message. When Issues change status email are also successfully sent. When I attempt to create a user or send an invitation no email is sent. This is a big challenge with getting acceptance in my organization. I could not find any smtp log to see what the error codes are. It would be nice to be able to review that in the Mail Queue - Error Queue.
You may want to try to turn on the email debugging to see what's going on.
I am not sure whether it will log it or not but it's worth a go.
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