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Jira for Outlook app Lost Connection Suddenly

Annette Byers
July 10, 2026

I purchased M365 for Jira app. I configured the “Jira for Outlook” app in Outlook and it worked fine last week. This week, I get an error message that I’m signed out of Jira (even though I’m not) and when I try to enter the “https://culpertechnology.atlassian.net/” URL and re-establish the connection, I receive an error message: Cannot connect to Jira

We couldn't connect to the Jira instance. At first, please make sure you have typed in the URL correctly.

If the URL is correct, the Jira system may not meet the technical requirements. If you have a self-hosted Jira instance, it needs to have our Jira Server Addon installed (and it needs to run on https). If you think this is an error, please contact our support.

I have tried EVERYTHING. It is very disappointing that this connection constantly fails. I want to configure it ONCE, and have it PERSIST.

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Brandon Viertel
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July 10, 2026

Morning @Annette Byers

We are using the M365 for Jira app as well, and as most features and functionalities are great. The part that we have struggled with is authentication via Outlook, which has been quite spotty. One of the issues we spent some time on was that it would say that we were not logged in, but were actually logged in with some form of broken authentication that was throwing errors. We eventually stumbled upon a dialogue for logout via the M365 connector (when attempting to use the Outlook Jira Create feature) and logged out, which fixed our connection issues. 

Can you post screenshots of your process, where you are accessing the M365 setup, and where you are receiving the error? 

Thanks!

Brandon

Annette Byers
July 10, 2026

Earlier this morning when I encountered the login issues, I removed the connection and attempted to re-establish the link to our Jira. I access the app from both the toolbar in Outlook and within the individual email toolbar. 

I enter my company URL and receive an error message (see screenshot). I have tried everything possible including uninstalling and re-installing everything on both the Jira and Outlook side. Nothing has worked.

 

Capture.PNGCapture-1.PNGCapture-2.PNGCapture-3.PNG

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