Two of our users are getting the AADSTS165000 error page when signing in at portal.office.com

Question

Two of our users are getting the AADSTS165000 error page when signing in at portal.office.com

ACollingwood 0

Hope this may be the correct area to post this - it's a bit of a mad one!

Two of our users (a staff member and pupil) are getting the following error when signing in to portal.office.com, OneDrive, or SharePoint on their iPad's browser...

AADSTS165000: Invalid Request: (The user session context is missing. One or more of the user context values (cookies; form fields; headers) were not supplied, every request must include these values and maintain them across a complete single user flow.

When I look at the sign-in logs against either user and find the sign-in failure, the error code I get is 399218.

This error appears to only happen on iPads (we've tested multiple iPads, too), and on both our Smoothwall Browser (based on Safari) and Google Chrome. No matter whether we clear the browser cache completely, fully wipe the iPad, or try private browsing, the error still persists.

Interestingly, when I sign in as a user that isn't having issues, then sign them out and sign the problematic user in, it works. I'm at a total loss as to what's causing the issue. There's no discernible difference between the working pupil account and the non-working account, either!

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Answer 1

Venkata Jagadeep 1,400 Microsoft External Staff Moderator

Hello ACollingwood,

We understand that few users are getting AADSTS165000 - Invalid request error while accessing Office applications.

And this issue is happening only while using iPads with Smoothwall browser and Google chrome.

You are able to access applications on the same platform and effected users are able to access when they sign-in after your activity.

This happens on iPad browsers as they fail to maintain session cookies during authentication flow. But in your case few users are able to access and issue is only with few users.

And let us know the behavior when the effected user tries to access through Edge browser instead of Safari.

And I request you to exclude the below Microsoft URLs from SmoothWall content filtering.

login.microsoftonline.com

login.live.com

*.office.com

*.microsoft.com

*.sharepoint.com

Please let me now if you have same kind of permissions on the device as other two users. (Do you have administrator permission on the device, and they have only user level permission)

Venkata Jagadeep 1,400 Reputation points Microsoft External Staff Moderator

2025-05-13T16:07:38.6566667+00:00

Hello ACollingwood,

Following up to see if the above answer was helpful. If this answers your query, do click Accept Answer and Yes for was this answer helpful. And, if you have any further query do let us know.
Venkata Jagadeep 1,400 Reputation points Microsoft External Staff Moderator

2025-05-14T02:27:38.3033333+00:00

Hello ACollingwood,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
ACollingwood 0 Reputation points

2025-05-14T08:31:29.35+00:00

Sadly still experiencing this issue. We've tried all of the above steps to no avail.
ACollingwood 0 Reputation points

2025-05-14T08:32:24.07+00:00

To clarify, I'm using the device as the student user, not as myself.
Venkata Jagadeep 1,400 Reputation points Microsoft External Staff Moderator

2025-05-16T08:26:03.72+00:00

Hello ACollingwood,

On the device side, I request you to check if the effected user is trying to access through a private session.

And on Safari Cookie Settings on iPad Go to Settings > Safari.

Ensure Prevent Cross-Site Tracking is disabled.

Ensure Block All Cookies is disabled.

And also I request you to check any Conditional Access policies are applying only for effected users with sign-in frequency and persistent browser session configuration.
Venkata Jagadeep 1,400 Reputation points Microsoft External Staff Moderator

2025-05-19T01:00:34.0266667+00:00

Hello ACollingwood,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.
Venkata Jagadeep 1,400 Reputation points Microsoft External Staff Moderator

2025-05-20T00:45:35.46+00:00

Hello ACollingwood,

We haven’t heard from you on the last response and was just checking back to see if you have a resolution yet. In case if you have any resolution please do share that same with the community as it can be helpful to others. Otherwise, will respond with more details and we will try to help.

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Two of our users are getting the AADSTS165000 error page when signing in at portal.office.com

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