Unable to authenticate Office365 secure IMAP/POP

[Anupam Panta]

I am using an outdated version of Jira, Jira v8.0.2, JIRA Service Desk Application v4.0.2.
I am unable to authenticate Office365 email from earlier this morning. We are using Secure IMAP for authentication. 

While trying with Secure IMAP, I am getting AUTHENTICATION FAILURE with the following error:

javax.mail.AuthenticationFailedException: AUTHENTICATE failed.
at com.sun.mail.imap.IMAPStore.protocolConnect(IMAPStore.java:727) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:366) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:246) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:267) [javax.mail-1.6.0.jar:1.6.0]
at com.atlassian.jira.internal.mail.processor.feature.channel.connectionverifier.DefaultChannelConnectionVerifier.verifyConnectionDefinition(DefaultChannelConnectionVerifier.java:60) [?:?]
at sun.reflect.GeneratedMethodAccessor2664.invoke(Unknown Source) [?:?]
at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) [?:1.8.0_181]
at java.lang.reflect.Method.invoke(Method.java:498) [?:1.8.0_181]
at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:343) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.eclipse.gemini.blueprint.service.importer.support.internal.aop.ServiceInvoker.doInvoke(ServiceInvoker.java:56) [?:?]
at org.eclipse.gemini.blueprint.service.importer.support.internal.aop.ServiceInvoker.invoke(ServiceInvoker.java:60) [?:?]
at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:185) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.springframework.aop.support.DelegatingIntroductionInterceptor.doProceed(DelegatingIntroductionInterceptor.java:136) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.springframework.aop.support.DelegatingIntroductionInterceptor.invoke(DelegatingIntroductionInterceptor.java:124) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.springframework.aop.framework.ReflectiveMethodInvocation.proceed(ReflectiveMethodInvocation.java:185) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.eclipse.gemini.blueprint.service.util.internal.aop.ServiceTCCLInterceptor.invokeUnprivileged(ServiceTCCLInterceptor.java:70) [?:?]
at org.eclipse.gemini.blueprint.service.util.internal.aop.ServiceTCCLInterceptor.invoke(ServiceTCCLInterceptor.java:53) [?:?]

I also tried with Secure POP, and weirdly got `unknown username or bad password` with the following error:

2022-10-11 15:06:33,772 ERROR [] http-nio-8080-exec-17 USERNAME 906x28893x1 1i25djp 110.44.125.18,127.0.0.1 /rest/servicedesk/1/servicedesk/IS/incomingemail/validateemailforcreation Unable to connect to the server at outlook.office365.com due to the following exception:
javax.mail.AuthenticationFailedException: Logon failure: unknown user name or bad password.
at com.sun.mail.pop3.POP3Store.protocolConnect(POP3Store.java:214) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:366) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:246) [javax.mail-1.6.0.jar:1.6.0]
at javax.mail.Service.connect(Service.java:267) [javax.mail-1.6.0.jar:1.6.0]
at com.atlassian.jira.internal.mail.processor.feature.channel.connectionverifier.DefaultChannelConnectionVerifier.verifyConnectionDefinition(DefaultChannelConnectionVerifier.java:60) [?:?]
at sun.reflect.GeneratedMethodAccessor2664.invoke(Unknown Source) [?:?]
at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) [?:1.8.0_181]
at java.lang.reflect.Method.invoke(Method.java:498) [?:1.8.0_181]
at org.springframework.aop.support.AopUtils.invokeJoinpointUsingReflection(AopUtils.java:343) [spring-aop-5.0.10.RELEASE.jar:5.0.10.RELEASE]
at org.eclipse.gemini.blueprint.service.importer.support.internal.aop.ServiceInvoker.doInvoke(ServiceInvoker.java:56) [?:?]
at org.eclipse.gemini.blueprint.service.importer.support.internal.aop.ServiceInvoker.invoke(ServiceInvoker.java:60) [?:?]

I understand Microsoft disabled IMAP with Modern Auth from October 1, 2022, IMAP was working till today, Oct 11, but as I mentioned we are using an outdated version, and it doesnot support Modern Auth. Secure IMAP was working 

[Brant Schroeder]

@Anupam Panta Welcome to the Atlassian community

This is due to Microsoft's deprecation of service as you pointed out and is discussed in the KB here: https://confluence.atlassian.com/jirakb/integrating-oauth-2-0-for-microsoft-accounts-on-jira-1188414154.html 

You are also correct that this is not supported in your version.  Without upgrading you will not be able to use the delivered services.

[Katelyn Macri]

Same issue here. We were moving to cloud but due to HIPAA issues we had to put it hold. Meanwhile, we are currently on Jira v8.16.1.  If we update to a newer version, will the issue be resolved so we can use Oauth 2.0? I'd really like to use email channels. Any idea what version we would need? 

thanks -