Jira Server throws AuthenticationFailedException when connecting to Exchange over SSL
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
Symptoms
JIRA is not retrieving mails from MS Exchange 2010 and the following appears in the atlassian-jira.log:
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2014-04-04 15:34:11,888 QuartzWorker-0 ERROR ServiceRunner Create Issue [atlassian.mail.incoming.mailfetcherservice] Create Issue [10000]: Error connecting to host 'mailserver.mycompany.com' as user 'niceuser' via protocol 'pop3': javax.mail.AuthenticationFailedException: Command is not valid in this state.
javax.mail.AuthenticationFailedException: Command is not valid in this state.Cause
JIRA is not being able to authenticate on the mail server because the SSL certificate of the mail server is not present in JIRA's keystore.
Resolution
Stop JIRA
Import the SSL Certificate of your mail server into JIRA's keystore (follow the instructions of connecting JIRA to SSL Services)
Start JIRA
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