Symptoms
Consider the following scenario:
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You are running Microsoft Outlook 2016 for Mac or Outlook for Mac 2011 connecting to a mailbox on a server that is running Microsoft Exchange Server.
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You have Digest Authentication enabled for Exchange Web Services (EWS) on the Exchange server.
In this scenario, you receive credential prompts in Outlook for Mac.
Cause
This issue occurs because using Outlook for Mac and Digest Authentication can cause authentication issues.
Resolution
To work around this issue, disable Digest Authentication for EWS on the Exchange server and use another authentication method, such as Windows Authentication.
More Information
The credential prompts caused by this issue may occur during the initial configuration of an Outlook Identity using Autodiscover, when Outlook is started by using a current Outlook Identity, or during Outlook use.