
AndresD.41025 (Customer) asked a question.
Ever since we enable WS-Federation for Office 365 we cannot sign in users to laptop when enrolling with autopilot.
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."
I have set up new rules for office 365 but can get the user to sign in. Following the below links
What should I check/re-configure?

Hi @AndresD.41025 (Customer) , Thank you for reaching out to the Okta Community!
There are a lot of variables to this type of implementation and without a proper overview of your current configuration there is not way to provide an on point answer, but I would start by looking at the configuration guide to check if the policies are set up correctly especially if you use Device Trust or Okta FastPass.
https://help.okta.com/oie/en-us/content/topics/apps/office365/win-autopilot/win-autopilot-integration.htm
The article you mentioned is also a good start, but only if you are experiencing the exact behavior mentioned there, otherwise I would hold off on making those specific policy configurations.
The Okta Community Questions forum isn't really meant for in-depth troubleshooting and
while I was looking into this issue I've noticed that you already have a Support ticket open.
I recommend continuing the discussion with the assigned Technical Support Engineers. They'll be able to access additional tools and resources to help you get to the bottom of it.
If my answer helped, remember to mark it as best to increase its visibility for other members of the Okta Community who might have the same questions as you.
Hope my answer helps!
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