Thank you, 6e0a867595f9, this helps. I verified it on our side, and seems like it doesn't work because of the misconfiguration of your Exchange server.
The context of the problem
Here are some technical details of what's going on.
In order to secure the connections between Outlook and Jira Cloud for Outlook add-in, Outlook provides us with a token that we use to sign all requests coming to our server. This token allows us to verify that the request is coming from you and not some attacker. In order to verify this token on our side, we need to load a public key available at your Exchange server. The URL we use to download that public key is also known as Autodiscover URL. More details about token validation here.
The reason the add-in doesn't work for you is that the Autodiscover URL of your Exchange server is not publically available and for that reason, we can't download the public key and verify the token.
How to fix the problem?
To make it work, your admins who manage the Exchange server, should make the Autodiscover URL either public or allow access to it from the IP addresses listed on this page (more specifically https://ip-ranges.atlassian.com).
Because this issue is publically available, I can't share the exact URL which is blocked, otherwise I'd expose your company's site. The structure of the URL is the following:
Here are more information about Autodiscover feature of Exchange server for your admins:
Let me know if that helps.
Hello 6e0a867595f9
Thanks for writing to us back.
I'm not sure why the /autodiscover/metadata/json/1 endpoint is not documented on that page but it's mentioned on this page about validating the identity token which we deal with in Jira Cloud for Outlook add-in.
Unfortunately, we do not control which Autodiscover URL to use from our side. The URL is provided securely in the identity token by Outlook and we read the URL from there.
I'd suggest you reach out to Microsoft support if you have any other questions about Autodiscover URL. They can provide more information about Autodiscover URLs and how to set them up for Outlook add-ins to work properly. Please let me know if you had a chance to resolve this issue on your side.