Fix Outlook Web Error 500: 'Something Went Wrong' Loop

Updated: 11/29/2025

You are trying to check your work or school email. You go to outlook.office.com, but the page flashes, reloads 5 times, and finally dies with: 'Something went wrong. Repeating redirects detected. Error 500.'. This is a server-side conflict where Outlook tries to log you in, realizes your cached 'Token' is expired, tries again, and gets stuck in a loop.

Method 1: The Token Flush (Browser)

Outlook stores aggressive cookies. You need to surgically remove them.

Step 1: Open Settings

In Chrome/Edge, go to chrome://settings/siteData.

Step 2: Search Outlook

Type outlook and office in the search bar.

Step 3: Delete All

Click the Trash icon next to every Microsoft-related entry. Restart the browser and log in again.

Method 2: Adjust System Time

Security tokens (Kerberos tickets) require your PC time to be perfectly synced with the Microsoft server. If you are off by even 2 minutes, login fails.

Step 1: Time Settings

Right-click your clock in the taskbar > Adjust date/time.

Step 2: Sync Now

Click the Sync now button. Ensure 'Set time automatically' is ON.

Method 3: Increase Mailbox Limits (Admins Only)

If you see 'MailboxNotEnabledForRESTAPI' or similar text in the error details, your user roles might be corrupted.

If you are the admin, go to the Exchange Admin Center and toggle the user's license off, wait 5 minutes, and toggle it back on to force a mailbox reprovision.