Outlook keeps asking for password (Something went wrong)

Symptoms:
Microsoft Outlook keep asking user for password. Upon entering the correct password, the password windows appears twice and then says 'something went wrong' - or - Trouble adding mailbox even though Office is activated

Resolution

  • *Check default browser - user may be signed in an account with alternative email address*
  • Clear temp files
  • Clear Windows Credentials related to O365
  • Make sure Office/Windows fully up to date
  • Settings > Accounts - Remove O365 account - Re-add (Uncheck 'Allow org to manage device')
  • Download the Support and Recovery Assistant for Office 365