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In Microsoft Outlook 2016 for Mac, you are repeatedly prompted for authentication while you're connected to your Office 365 account.
This issue occurs because of the presence of duplicate tokens in the keychain.
To resolve this issue in Outlook 2016 for Mac, install the February 2017 Outlook update (version 15.31.0) from the following Office website:
To work around this issue, delete any cached passwords for your account, and also delete any modern authentication tokens from the keychain. To do this, follow these steps.
Note
These steps affect all Office applications that use modern authentication.
Quit Outlook and all other Office applications.
Start Keychain Access by using one of the following methods:
In the search field in Keychain Access, enter Exchange.
In the search results, select each item to view the Account that's listed at the top, and then press Delete. Repeat this step to delete all items for your Exchange account.
In the search field, enter adal.
Select all items whose type is MicrosoftOffice15_2_Data:ADAL:<GUID>, and then press Delete.
They may not be compatible with your version of macOS.Uninstall any app plug-ins or enhancements from other manufacturers.If you recently updated the app or macOS, a plug-in or enhancement you installed may no longer be compatible.to learn whether hardware you installed, such as additional memory, is incompatible, improperly installed, or defective. There may be a problem with the original file.to your software.Disconnect any peripheral devices you just connected (for example, a printer). You may lose unsaved changes.If the app quit, reopen it by clicking Reopen in the dialog that appears.Restart your Mac by choosing Apple menu Restart.Check the app’s documentation to see whether it’s compatible with your version of macOS.Open another file in the app. .If the app is frozen and unresponsive, choose Apple menu Force Quit, select the app in the dialog that appears, then click Force Quit.
In the search field, enter office.
Select the items that are named Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2, and then press Delete.
Quit Keychain Access.
Note
When you start Outlook, you are prompted to authenticate.