Sending outgoing mail always fails

[Stefan]

We're running JIRA Service Desk on a Ubuntu 18.04 server and using Office 365 for our Emails. We've configured JIRA to use Office 365 direct send (https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-office-3 - Option 2) to send outgoing emails. The test email in the JIRA configuration will always get send successfully.

All other mails will end up in the error mail queue. In the error mail queue I can't see the actual error message and per your documentation we enabled Outgoing Mail log as well as Outgoing Mail debug. But the corresponding file atlassian-jira-outgoing-mail.log is never created so we have not idea what the issue is.

[Rakesh Kumar]

Hi Stefan, 

If you have configured outgoing mails using option 2 then i believe you have not missed the condition that email receivers must have Office 365 accounts only and must belong to the same organisation which configured mailbox belongs.  Did you also try to send a mail through any jira issue to the same mailbox configured? 

You can also go through atlassian-jira.log for further investigation. You can also reach to Atlassian support team with support.zip file. 

Regards, 

Rakesh