IMAP setup fails with AUTHENTICATE Failed error in logs in Jira server when using OAuth
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
Problem
When trying to set up an IMAP service for JIRA applications notifications, you get an error AUTHENTICATE Failed. After enabling mail debugging, the following appears in the logs:
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[Alerts Incident] Caesium-1-3 anonymous Incident ITSM * OK The Microsoft Exchange IMAP4 service is ready. [QWxhZGRpbjpvcGVuIHNlc2FtZQ==]
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM IUR0 CAPABILITY
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM * CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS MOVE ID UNSELECT CHILDREN IDLE NAMESPACE LITERAL+
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM IUR0 OK CAPABILITY completed.
IMAPS: AUTH: PLAIN
IMAPS: AUTH: XOAUTH2
IMAPS: protocolConnect login, host=outlook.office365.com, user=user_name@atl.onmicrosoft.com, password=<non-null>
IMAPS: AUTHENTICATE PLAIN command trace suppressed
IMAPS: AUTHENTICATE PLAIN command result: IUR1 NO AUTHENTICATE failed.
IMAPS: trying to connect to host "outlook.office365.com", port 993, isSSL true
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM * OK The Microsoft Exchange IMAP4 service is ready. [QWxhZGRpbjpvcGVuIHNlc2FtZQ==]
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM IUS0 CAPABILITY
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM * CAPABILITY IMAP4 IMAP4rev1 AUTH=PLAIN AUTH=XOAUTH2 SASL-IR UIDPLUS ID UNSELECT CHILDREN IDLE NAMESPACE LITERAL+
[Alerts Incident] Caesium-1-3 anonymous Incident ITSM IUS0 OK CAPABILITY completed.
IMAPS: AUTH: PLAIN
IMAPS: AUTH: XOAUTH2
IMAPS: protocolConnect login, host=outlook.office365.com, user=user_name@atl.onmicrosoft.com, password=<non-null>
IMAPS: AUTHENTICATE PLAIN command trace suppressed
IMAPS: AUTHENTICATE PLAIN command result: IUS1 NO AUTHENTICATE failed. The following warning will also be in the atlassian-jira-incoming-mail.log:
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WARN [Alerts Incident] Caesium-1-3 anonymous Incident ITSM Incident ITSM [10900]: javax.mail.AuthenticationFailedException: AUTHENTICATE failed. while connecting to host "outlook.office365.com" as user "user_name@atl.onmicrosoft.com" via protocol "SECURE_IMAP": javax.mail.AuthenticationFailedException: AUTHENTICATE failed.
javax.mail.AuthenticationFailedException: AUTHENTICATE failed.
at com.sun.mail.imap.IMAPStore.protocolConnect(IMAPStore.java:708) [jakarta.mail-1.6.5.jar:1.6.5]
at javax.mail.Service.connect(Service.java:364) [jakarta.mail-1.6.5.jar:1.6.5]
at javax.mail.Service.connect(Service.java:222) [jakarta.mail-1.6.5.jar:1.6.5]
at javax.mail.Service.connect(Service.java:243) [jakarta.mail-1.6.5.jar:1.6.5]
at com.atlassian.mail.server.InternalAuthenticationContext.connectService(InternalAuthenticationContext.java:58) [atlassian-mail-5.0.3.jar:?]
at com.atlassian.mail.server.AbstractMailServer.smartConnect(AbstractMailServer.java:156) [atlassian-mail-5.0.3.jar:?]
at com.atlassian.jira.service.services.mail.MailServicesHelper.lambda$connectUsing$2(MailServicesHelper.java:81) [jira-api-8.13.3.jar:?]
at java.util.Optional.map(Optional.java:215) [?:1.8.0_181]
at com.atlassian.jira.service.services.mail.MailServicesHelper.handleAuthAwareMailServer(MailServicesHelper.java:52) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.mail.MailServicesHelper.getConnectedStore(MailServicesHelper.java:46) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.mail.MailFetcherService.getConnectedStore(MailFetcherService.java:397) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.mail.MailFetcherService$MessageProviderImpl.getAndProcessMail(MailFetcherService.java:166) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.mail.MailFetcherService.processMessages(MailFetcherService.java:361) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.mail.MailFetcherService.runImpl(MailFetcherService.java:353) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.services.file.AbstractMessageHandlingService.run(AbstractMessageHandlingService.java:229) [jira-api-8.13.3.jar:?]
at com.atlassian.jira.service.JiraServiceContainerImpl.run(JiraServiceContainerImpl.java:68) [classes/:?]
at com.atlassian.jira.service.ServiceRunner.runService(ServiceRunner.java:62) [classes/:?]
at com.atlassian.jira.service.ServiceRunner.runServiceId(ServiceRunner.java:44) [classes/:?]
at com.atlassian.jira.service.ServiceRunner.runJob(ServiceRunner.java:32) [classes/:?]
at com.atlassian.scheduler.core.JobLauncher.runJob(JobLauncher.java:134) [atlassian-scheduler-core-3.0.0.jar:?]
at com.atlassian.scheduler.core.JobLauncher.launchAndBuildResponse(JobLauncher.java:106) [atlassian-scheduler-core-3.0.0.jar:?]
at com.atlassian.scheduler.core.JobLauncher.launch(JobLauncher.java:90) [atlassian-scheduler-core-3.0.0.jar:?]
at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.launchJob(CaesiumSchedulerService.java:435) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeClusteredJob(CaesiumSchedulerService.java:430) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeClusteredJobWithRecoveryGuard(CaesiumSchedulerService.java:454) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeQueuedJob(CaesiumSchedulerService.java:382) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeJob(SchedulerQueueWorker.java:66) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeNextJob(SchedulerQueueWorker.java:60) [atlassian-scheduler-caesium-3.0.2.jar:?]
at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.run(SchedulerQueueWorker.java:35) [atlassian-scheduler-caesium-3.0.2.jar:?]
at java.lang.Thread.run(Thread.java:748) [?:1.8.0_181]Cause
Using the wrong Scopes can cause this error, even when the authentication attempt looks successful in the related Google or Microsoft logs.
Resolution
Use the Scopes listed in Integrating with OAuth 2.0.
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For Google, we recommend using the https://mail.google.com/ scope for IMAP and POP3.
For Microsoft, we recommend https://outlook.office.com/IMAP.AccessAsUser.All or https://outlook.office.com/POP.AccessAsUser.All, and offline_access.Updated on April 8, 2025
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