Forum Discussion
**bleep**. Security Update (like KB5101650) breaking SmartCard Authentication for Office 2024 apps to O365
Looking for some support on this issue. I have Win11 clients that were upgraded from 24H2 to 25H2 last year. They were functioning well until earlier this year when the Cumulative Updates started breaking smartcard authentication on our clients (day after installing/rebooting/cache clearing). This seems to be a known issue but are there any real fixes? Symptom is that after the update is installed, next day (after a reboot or cache cleared) the user starts their Outlook or Teams application, when receiving the prompt that says "you will be prompted for your PIN" nothing follows, you will see the blue dots circling and after 5 or so minutes it times out. Clicking on the "..." shows an informational message error #50058, which says that not enough information was provided. The authentication process is failing... BTW - web authentication works just fine, it's just the local application (Teams, Outlook, etc.) that fail.
I found that creating a new account on the system seems to work just fine, but for people that have established accounts and program environments that are setup for them to work, creating a new account is very unappealing to them. I'd like to be able to just get their current accounts working. Creating a new profile, wiping current profile info from registry doesn't seem to work thanks to automagic backups the OS is doing, but even that would still require setting up a new profile and copying over non AAPDAT file structure info... Does Microsoft not have a fix to this "known" issue? I spent a few weeks really digging into this and the best I can find as a work around is to disable the automatic backups of the NTUSER.DAT, blow away current profile info in registry, rename current profile structure, and then have the user login "anew". Again, this still requires a copy of the non-AAPDAT data back into the new structure (at least permissions won't be an issue) but that will not restore all application-based information for that user--that still will have to be re-created, which I think the users will not want to do because it means starting over from scratch.
2 Replies
Seems this is well known but not hotfix yet, the workaround:
1. Profile Recreation
Disable automatic NTUSER.DAT backups
Delete cached profile registry keys under HKLM\SOFTWARE\Microsoft\Windows NT\CurrentVersion\ProfileList
Rename the existing profile folder, then let Windows create a fresh one at next login
Copy non-AppData files back manually
Note: Application-specific settings must be reconfigured.
2. Clear Cached Credentials
Open Credential Manager > Windows Credentials
Remove old Office/ADAL/WAM entries
Disconnect stale work accounts under Settings > Accounts > Access work or school
Reboot and re-sign in interactively
3. Interactive Sign-In Reset
Close affected apps
Sign in at office.com with SmartCard PIN
Relaunch Outlook/Teams to refresh the Entra session
Web authentication succeeding, a new Windows profile working, and established profiles failing with AADSTS50058 isolate the problem to per-user desktop sign-in state. Microsoft defines 50058 as insufficient session information for single sign-on, while Microsoft 365 desktop apps use the per-user Web Account Manager broker. That does not by itself prove the cumulative update broke smart-card authentication. On an affected profile, first run the Microsoft 365 sign-in troubleshooter. Reproduce once and capture the Entra sign-in log’s correlation ID, timestamp, failure details, and the AppModel-State or AAD operational events. In PowerShell running as that user, check Get-AppxPackage Microsoft.AAD.BrokerPlugin. If it is missing or its Work or school account window will not open, use Microsoft’s documented Add-AppxPackage -Register repair for that system package, restart, and retest. Do not delete NTUSER.DAT or rebuild more profiles. If the failure returns after a specific KB, open a Microsoft support case with those logs and exact builds