SMTP Error : Caused by: javax.mail.AuthenticationFailedException: 535 5.7.139 Authentication unsuccessful
Platform Notice: Data Center Only - This article only applies to Atlassian products 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
Environment
Jira Data Center.
SMTP Mail Server configuration with TLS enabled.
Microsoft SMTP.
Diagnosis
Checking the Outgoing Mail logs we can see the error
log
1
Caused by: javax.mail.AuthenticationFailedException: 535 5.7.139 Authentication unsuccessful, the request did not meet the criteria to be authenticated successfully. Contact your administrator. [XXXXXXXXXXXXX.XXXXXXXX.PROD.OUTLOOK.COM 2024-07-23T16:45:06.873Z 08DCA64B22408C5C]Cause
Microsoft enabled the policy Multifactor authentication for per-user multifactor authentication users for security reasons.
Solution
Disable the security policy Multifactor authentication for per-user multifactor authentication users
For reference: Microsoft-managed policies
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