Hi Artem. That usually works as expected every time. It's a major Okta integration, and I haven't seen it behave like that before so it's either environmental or ( most likely ) the permissions for the account you are logging into O365 with are not sufficient. Those are where I would start, but best raise a ticket with Okta as they can see more of what happens than the Okta logs you can see.

Although do the Okta logs show anything for the event ?

Hi Niall,

Thank you for your swift reply and the suggestions. It does not seem that the error gets logged in the Okta logs. Regarding the permissions, I'm Accepting the Application permissions using a Global Administrator, so the permissions should be sufficient. The Application gets created in Azure Active Directory as well, but Okta just shows the error mentioned above, reauthentication does not work without recreating the whole Okta App. Maybe it's a limitation with the Okta Dev Tenant I'm using?

Could you possibly point me to the place where I can open up an Okta Support Request? The only thing I found so far is this help forum. 🙂

Just a few more things to try if you haven't already. If you log into O365 with multiple accounts, it can get a little messed up. So do the usual things about trying a different ( isolated ) browser, clear down cache etc and retry. A 503 is fairly unusual in Okta. What is happening there is effectively an exchange of tokens between Okta and Azure to allow Okta the relevant permissions on the APIs.

One follow up, is this a dev/free tenant ? You might find some restrictions on LCM ( lifecycle management ) functionality if that's the case. Either way, a ticket will get you the answer.

https://support.okta.com/help/s/article/How-to-Create-a-Support-Case?language=en_US

Or at the bottom of this page if you are an authenticated user, there should be a green button saying 'Get Support'