Unable to add Incoming Mail (POP/IMAP) Mail server on v8.5.4

[Danny]

I am using Atlassian Jira Project Management Software v8.5.4.

I cannot authenticate our Microsoft 365 email account inside JIRA setting.

Incoming Mail > POP/IMAP Mail Servers > Add POP/IMAP mail server

Error 

Unfortunately no connection was possible. Review the errors below and rectify:

• AuthenticationFailedException: AUTHENTICATE failed.

[Pavel Junek · Accepted solution]

Hi Danny,

Welcome to Atlassian community!

Can you check Jira log file? There is more information about the problem. You can check this Atlassian article - IMAP setup fails with AUTHENTICATE Failed error in logs in Jira server when using OAuth or you can check another Community threat - AuthenticationFailedException: AUTHENTICATE failed during test of OAuth2.0 Exchange connection 

Cheers!

Pavel

[Danny]

HI Pavel,

Please see the logs. I am still having issue. I would appreciate step by steps guide.

atlassian-jira-incoming-mail.log

2023-04-20 11:40:39,598+0800 ERROR [] Caesium-1-2 ServiceRunner     Messaging Error when MailPullerWorker pulls emails from account@example: AUTHENTICATE failed.

2023-04-20 11:40:40,864+0800 ERROR [] Caesium-1-2 ServiceRunner     Messaging Error when MailPullerWorker pulls emails from account@example: AUTHENTICATE failed.

atlassian-jira.log

2023-04-20 11:45:03,113+0800 http-nio-8080-exec-19 ERROR test 705x5125272x1 1oqlzar 192.168.0.3,0:0:0:0:0:0:0:1 /test/admin/VerifyPopServerConnection!update.jspa [c.a.j.p.mail.webwork.VerifyMailServer] Unable to connect to the server at outlook.office365.com due to the following exception: javax.mail.AuthenticationFailedException: AUTHENTICATE failed.
[root@test log]#

[Pavel Junek]

Hi Danny,

it looks like firewall issues or login/password issue.

You can try check firewall -> test via command telnet outlook.office365.com 995 from server side.

Source: https://community.atlassian.com/t5/Jira-questions/JIRA-couldn-t-connect-to-outlook-office365-com-Check-and-make/qaq-p/1768175 

Pavel

[Danny]

Hi Pavel,

There is no issue with firewall and connection to Microsoft is working.

[root@test test]# telnet outlook.office365.com 993
Trying 40.99.10.18...
Connected to outlook.office365.com.

We are using Jira v8.5.4

Can you confirm this version can authenticate Microsoft365 account? 

[Pavel Junek]

Hi Danny,

Thank you for your information.
Unfortunately, I am not able to confirm whether your Jira can connect to Office 365, but I think it shouldn't be a problem.

Are you entering the wrong credentials?

You can try to contact the official Atlassian support. But your version of Jira is already very outdated (EOL).

Pavel

[Danny]

Hi Pavel, Atlassian support is not supporting us anymore since we don't have active contract. Any other idea in your mind? we are pretty much on our own.

[Pavel Junek]

Hi Danny,

Ah, I see. Thank you for info. 

It seems, Microsoft disable Basic authentication for mail configuration and you need configure incoming mail only through OAuth 2.0

I found this Atlassian article . Unfortunately, Atlassian add support for OAuth 2.0 since Jira 8.5.9 (+ other add functionality since Jira 8.5.12) (Jira 8.5 was LTS Jira version).

• Jira Software 8.5.x release notes 
• https://jira.atlassian.com/browse/JRASERVER-63917 
• https://jira.atlassian.com/browse/JRASERVER-72033 

Officially was support for OAuth 2.0 in mail handlers has been shipped within Jira 8.10. 

So my guess is that you won't be able to connect to Microsoft 365 without the upgrade in Jira 8.5.4 version.

Pavel

[Danny]

HI Pavel, thanks for information.