Jira Data Center Azure Communication Services outgoing mail fails
Platform Notice: Data Center Only - This article only applies to Atlassian apps on the Data Center platform.
Note that this KB was created for the Data Center version of the product. Data Center KBs for non-Data-Center-specific features may also work for Server versions of the product, however they have not been tested. Support for Server* products ended on February 15th 2024. If you are running a Server product, you can visit the Atlassian Server end of support announcement to review your migration options.
*Except Fisheye and Crucible
Summary
When Azure Communication Services is configured as the outgoing SMTP mail server for Jira Data Center and the connection test is run, Jira displays the errors “Username or password incorrect” or “502 5.3.3 Command not implemented” even though the correct credentials have been provided.
Diagnosis
With outgoing email debugging enabled, log messages similar to the following can be seen in the outgoing mail log:
2025-01-01 00:00:00,000+0000 DEBUG [localhost] http-nio-8080-exec-1 username 123x456789x0 123abcd 127.0.0.1 /secure/admin/VerifySmtpServerConnection!update.jspa [c.atlassian.mail.outgoing] NOOP
2025-01-01 00:00:00,100+0000 DEBUG [localhost] http-nio-8080-exec-1 username 123x456789x0 123abcd 127.0.0.1 /secure/admin/VerifySmtpServerConnection!update.jspa [c.atlassian.mail.outgoing] 502 5.3.3 Command not implementedCause
Jira sends an SMTP NOOP command during the connection test, and Azure Communication Services does not support this command.
Solution
To resolve this problem, we need to configure Jira's mail library to use the RSET command instead of the NOOP command for connection testing:
Add the following system property to Jira's startup parameters:
-Dmail.smtp.userset=trueRestart Jira.
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