Using older versions of Outlook for Mac for personal email and calendar
For Outlook on Mac, repeated account lock or repeated sign-in prompts in the provided scenarios are tied to a few known causes:
- Duplicate or stale authentication tokens in macOS Keychain
Outlook 2016 for Mac can repeatedly prompt for authentication because of duplicate tokens in Keychain. The documented workaround is:
- Quit Outlook and all Office apps.
- Open Keychain Access.
- Search for Exchange and delete entries for the affected account.
- Search for adal and delete items of type MicrosoftOffice15_2_Data:ADAL:<GUID>.
- Search for office and delete Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2.
- Restart Outlook and authenticate again.
- Wrong username format for federated Microsoft 365 sign-in If the mailbox uses modern authentication with a federated account, repeated prompts can occur when the email address is entered instead of the UPN in Outlook’s Accounts dialog. The documented fix is to enter the UPN in the User name field, then quit and restart Outlook.
- Keychain permission problems If Office for Mac repeatedly asks for keychain access or sign-in every launch, Office may have been moved from the default /Applications folder, or keychain permissions may need to be restored. The documented first step is to select Always Allow when prompted. If that does not hold, quit all Microsoft 365 for Mac apps and restore keychain permissions using Apple’s keychain access steps.
- A specific Microsoft 365 Plan1 authentication issue
There is also a documented Outlook for Mac issue where authentication fails because Outlook tries to connect to Teams for free/busy data when there is no Teams license. That article states this occurs with a Microsoft365 P1 license and the fix is to run this Terminal command after quitting Outlook:
defaults write com.microsoft.Outlook ClassicCalendarDisableMsTeamsMeeting -int 1
Because this is a Microsoft 365 Family / home scenario, the most relevant documented paths are the Keychain token cleanup and Keychain permission checks first.
A practical order is:
- Quit Outlook and all Office apps.
- In Keychain Access, remove the affected Outlook/Exchange, adal, and office identity cache items as documented.
- Reopen Outlook and sign in again.
- If macOS prompts for keychain access, choose Always Allow.
- If prompts continue every launch, restore keychain permissions.
- If the account is an Outlook.com account that becomes temporarily blocked, the documented unblock action is to reset the password.
If the account itself is being blocked because of unusual sign-in activity, the documented Outlook.com action is password reset to unblock the account.
- Outlook 2016 for Mac repeatedly prompts for authentication
- You're repeatedly prompted for credentials when using modern authentication in Outlook 2016 for Mac
- Office for Mac repeatedly requesting keychain access | Microsoft Support
- Unblock my Outlook.com account | Microsoft Support
- Fix authentication issue in Outlook for Mac when connecting to an Office 365 Plan1 service | Microsoft Support