
User16660455422456237991 (Customer) asked a question.
Ever since transitioning to Okta SSO, users are unable to sign on to Windows devices.
Users on the OOBE "Sign in with Microsoft" Screen input their login information, and are redirected to an Okta login page. They are able to hit enter and login, but are never prompted to authenticate. They are then sent back to the previous page with an error message reading "We couldn't sign you in. Please try again."
When I go to check the user logs, there is are at least 10-15 entries of two events that read "Evaluation of sign-on policy allow" and "User single sign on to app success."
What should I check/re-configure?
Thanks

@User16660455422456237991 (Customer) - You posted your question in the Workflows (product) section when it appears you are having issues with Single Sign-on (SSO). I suggest re-posting your question to the correct group as you will likely receive a helpful response.
Hi @User16660455422456237991 (Customer) , Thank you for reaching out to the Okta Community!
Perhaps double-check that your use case is supported as per the following:
https://help.okta.com/oie/en-us/Content/Topics/Apps/Office365/win-autopilot/win-autopilot-supported-cases.htm
I've seen some mentions of this being cause by misconfiguration and they solved it by adding a custom useragent string with request.userAgent.contains("Windows-AzureAD-Authentication-Provider") and adjustin O365 sign on policy.
There is also tangential mention of a "supportsmfa=true" being required in the following post mentioning a similar loop situation.
https://support.okta.com/help/s/question/0D54z00006wnSxKCAU/using-okta-for-hybrid-aad-join-windows-hello-for-bussiness?language=en_US
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Hope my answer helps!
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@User16660455422456237991 (Customer) - I'll also be removing your other post due to it being a duplicate. Sorry for the confusion.