Jira for Outlook app Lost Connection Suddenly

Hi @Annette Byers ,

this is Benjamin from yasoon, the company behind the Jira for Outlook app.

Thank you for posting into the community!

Since you opened a ticket in our JSM queue we encourage you communicating with us via the ticket and we will keep the community here posted about the progress.

Please be aware that what Anwesha Pan posted is more related to the official Jira Cloud for Outlook app not our app. However, some of the tips might work. 

Thanks to all of you for helping out here :)

Best regards,

Benjamin

Hi @Annette Byers 👋🏻

First of all, welcome to community! ✨

Since it worked last week and broke this week, this might be an authentication token expiry or SSO session issue — not a URL problem. You could try the below troubleshooting steps:

1. SSO / Authentication Session Issue 

1. Open an incognito/private browser window

2. Go to id.atlassian.com and log in with your credentials

3. Click the "Continue" button (the blue one) — do not click the Microsoft/SSO icon

4. Complete authentication fully

5. Then go back to Outlook and try connecting the add-in again

This workaround resolves a known issue where OAuth/SSO tokens become stale and the add-in can't re-establish the session. https://jira.atlassian.com/browse/API-715

2. Clear the Add-In's Cached Credentials

Even after reinstalling, the add-in may retain cached auth data:

• In Outlook, go to File → Office Account → Connected Services and remove any Jira-related connections

• Clear your browser cache and cookies (Outlook Web uses the browser engine for add-ins)

• If using Outlook Desktop on Windows, clear the Office Add-in cache: delete contents of %LOCALAPPDATA%\Microsoft\Office\16.0\Wef\

3. Check the M365 for Jira App Status on the Jira Side

Go to culpertechnology.atlassian.net → ⚙ Settings → Apps → Manage Apps and verify:

• The M365 for Jira app is still enabled and the license is active

• There are no warnings or errors on the app's configuration page

• The app hasn't been updated recently (updates can sometimes reset OAuth grants)

4. Re-Authorize via Outlook Web (Not Desktop)

The Outlook desktop app has known limitations with add-in auth flows. Try this:

1. Open Outlook on the web (outlook.office.com)

2. Open any email → click the Apps icon → launch the Jira add-in

3. Click Connect Now and complete the authorization from the web version

4. Once connected in Outlook Web, return to Outlook Desktop — the session should carry over

I hope this helps & resolves your issue. 🙂

Thanks,
Anwesha

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