I post this here, since other people might find the info useful:
Can someone at Atlassian please confirm or deny the following as being a bug?
In JIRA 5.1, setting Outgoing mail to be delivered via an MS Exchange server that only permits NTLM authentication, sending fails with Authentication Failed, even with correct credentials. Setting the startup option pertaining to auth domain has no effect.
Replacing atlassian-jira/WEB-INF/lib/mail-1.4.6.jar with version 1.4.1 resolves the problem.
It seems to me, that either there is a bug in JavaMail 1.4.6 *or* there is a bug in JIRA 5.1 regarding its use of JavaMail 1.4.6 - it being possible that something changed between 1.4.1 and 1.4.6 regarding how to make use of the library.
There was a modification in mail-1.4.6 which prevents the NTLM to work as it should. As I've seen, it works for many Exchange servers, but for some, it doesn't. All this is detailed on the bug JRA-27623.
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