Jira for Outlook app Lost Connection Suddenly

Question

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.

Benjamin Linser _yasoon_ · Answer

Short update: After trying to troubleshoot this it was suddenly working again. We originally thought this happened because of an internal change (e.g. a VPN, proxy or restrictions regarding the connection within the network between Outlook and the Jira system).

Unfortunately we are not able to track this done anymore. If any of you encountering a similar issue please feel free to reach out to us so we can help you here: yasoon Support - Jira Service Management

Thank you all!

Benjamin Linser _yasoon_ · Answer

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

Anwesha Pan · Answer

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

Open an incognito/private browser window

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

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

Complete authentication fully

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:

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

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

Click Connect Now and complete the authorization from the web version

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

I hope this helps & resolves your issue. 🙂

Thanks,
Anwesha