• Outlook 2016 For Mac Not Syncing
• Outlook 2016 For Mac Keeps Asking For Password

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Symptoms

May 20, 2019  In Microsoft Outlook 2016 for Mac, when you navigate to a folder in which several encrypted email messages are displayed in the message list, Outlook freezes or experiences other performance issues. We are having some pain around Office/Outlook 2016 for Mac as opposed to the experience with OWA and Outlook 2016 for Windows. Specifically, we need the ability to open another user's calendar from the address book, without needing to setup sharing/permissions/etc. This is 100% possible in Outlook 2016 for Windows as well as OWA.

In Microsoft Outlook 2016 for Mac, you are repeatedly prompted for authentication while you're connected to your Office 365 account.

Cause

This issue occurs because of the presence of duplicate tokens in the keychain.

Resolution

To resolve this issue in Outlook 2016 for Mac, install the February 2017 Outlook update (version 15.31.0) from the following Office website:

Workaround

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

Outlook 2016 For Mac Not Syncing

These steps affect all Office applications that use modern authentication.

Outlook 2016 For Mac Keeps Asking For Password

1. Quit Outlook and all other Office applications.

2. Start Keychain Access by using one of the following methods:

   • Select the Finder application, click Utilities on the Go menu, and then double-click Keychain Access.
   • In Spotlight Search, type Keychain Access, and then double-click Keychain Access in the search results.

3. In the search field in Keychain Access, enter Exchange.

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4. In the search results, select each item to view the Account that's listed at the top, and then press Delete. Lumion for macintosh. Repeat this step to delete all items for your Exchange account.

5. In the search field, enter adal.

6. Select all items whose type is MicrosoftOffice15_2_Data:ADAL:<GUID>, and then press Delete.

7. In the search field, enter office.

8. Select the items that are named Microsoft Office Identities Cache 2 and Microsoft Office Identities Settings 2, and then press Delete.

9. Quit Keychain Access.

   Note

   When you start Outlook, you are prompted to authenticate.