Office / Microsoft 365 “Something went wrong” sign-in error after Windows updates

Hello community,

Posting this because I spent quite a bit of time tracking down a resolution.

If you are trying to activate Office, sign into Microsoft 365 desktop applications, or simply add a Microsoft work account and receive only “Something went wrong. Please try again.” with no useful error code, this may be worth checking.

In my case:

• Microsoft 365 worked normally in a browser.
• Office desktop applications would not authenticate.
• Reinstalling/repairing Office did not resolve the problem.
• SFC and DISM did not resolve it.
• Clearing OneAuth, TokenBroker, IdentityCache, and AAD BrokerPlugin data did not resolve it.
• Microsoft.AAD.BrokerPlugin itself was installed and reported Status: OK.

Reviewing the Microsoft-Windows-AAD/Operational log showed errors including:

• 0xCAA100D8
• A login hint was sent that doesn't match any WebAccount in the system.

I also found an old/stale Microsoft Entra registered device object for the computer in the Entra admin center.

This computer intentionally uses a local Windows account and is not supposed to be Entra joined, Entra registered, or Intune managed.

What ultimately resolved the problem was:

1. Remove the stale device registration from Microsoft Entra ID

I located the affected computer under Entra ID → Devices and deleted the stale Microsoft Entra registered device object.

2. Prevent Windows from attempting Workplace Join on this PC

From elevated PowerShell:

New-Item -Path "HKLM:\SOFTWARE\Policies\Microsoft\Windows\WorkplaceJoin" -Force | Out-Null
 
New-ItemProperty `
 -Path "HKLM:\SOFTWARE\Policies\Microsoft\Windows\WorkplaceJoin" `
 -Name "BlockAADWorkplaceJoin" `
 -PropertyType DWord `
 -Value 1 `
 -Force

This creates:

• HKLM\SOFTWARE\Policies\Microsoft\Windows\WorkplaceJoin
• BlockAADWorkplaceJoin = 1

After rebooting, Microsoft 365/Office authentication began working normally again.

Important: I would only recommend this workaround where the computer is intentionally supposed to remain a local/unmanaged device. Do not blindly apply BlockAADWorkplaceJoin to computers that are supposed to be Microsoft Entra registered/joined or managed through Intune.

Hopefully this saves someone else the troubleshooting time.