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In Outlook, click Help Check For Updates. If an update is found, download and install it. Restart Outlook. If the problem continues, click Help Contact Support.

Symptoms

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:

Outlook

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

These steps affect all Office applications that use modern authentication.

  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.

  4. 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.

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  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.

If you are having problems with your email, one common diagnostic aid is a complete list of the message's headers. Headers show the path a message took to get from the sender to the recipient. The IT Service Desk or other technical support may ask you to provide a message's headers.

  1. Right-click (or ctrl-click) the message in your Inbox or other folder (do not open the message).
  2. From the menu that appears, select View Source.

Your text editor (typically an application called TextEdit) will open, displaying all the headers for the message, followed by the message body.

If you need to copy the headers (to paste somewhere else),

  1. Drag over the text from the beginning of the text to the beginning of the body of the message.
  2. Press command-c on your keyboard; this copies the highlighted text to the clipboard.
  3. Then, with an email message or other document open, press command-v to paste the header text into that document.