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You might not have all the virtual directories configured correctly.<br />
Post the results of:<br />
<br />

<pre><code class="code-1 nolinks" id="code-20-42349346-1"><span>Get-OabVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*</span>
<span>Get-WebServicesVirtualDirectory | fl server, Name,ExternalURL, InternalURL, *auth*</span>
<span>Get-EcpVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*</span>
<span>Get-ActiveSyncVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*</span>
<span>Get-OutlookAnywhere | fl server, Name, *hostname*, *auth*</span>
<span>Get-OwaVirtualDirectory | fl server, Name, ExternalURL, InternalURL, *auth*</span>
<span>Get-ClientAccessService | fl Name,OutlookAnywhereEnabled, AutodiscoverServiceInternalUri</span>
<span>Get-ExchangeCertificate | fl FriendlyName, Subject, CertificateDomains, Thumbprint, Services, Issuer, *not*</span>
<span>Get-MapiVirtualDirectory | fl server, Name,ExternalURL,InternalURL, *auth*</span>
</code></pre>
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Another possibility might be poor connectivity. If the connection between the client and server is going up and own, you will see sporadic password prompts.
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One thing to check is the full autodiscovery setup as this can be the reason (and usually is) for password prompts.<br />
<br />
You need to make sure your OutlookAnywhere and AutoDiscover settings are setup properly along with Split-DNS. <br />
<br />
<a href="https://garzafx.com/2014/05/05/fix-for-outlook-20102013-prompts-for-user-id-and-password-after-migrating-to-exchange-2013/" rel="ugc">https://garzafx.com/2014/05/05/fix-for-outlook-20102013-prompts-for-user-id-and-password-after-migrating-to-exchange-2013/</a><br />
<br />
Hope this helps!
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No comment has been added to this question in more than 21 days, so it is now classified as abandoned.<br />
<br />
I have recommended this question be closed as follows:<br />
<br />
Accept: roeuyc (<a href="https:#a42365177" rel="ugc">https:#a42365177</a>)<br />
<br />
If you feel this question should be closed differently, post an objection and the moderators will review all objections and close it as they feel fit. If no one objects, this question will be closed automatically the way described above.<br />
<br />
seth2740<br />
Experts-Exchange Cleanup Volunteer
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<div class="content wysiwyg-content">
Hi there, <br />
<br />
There are many users outlook 2013 complain about repeatedly password prompts after migrated to exchange 2016. It must be a bug of outlook 2013, and it has resolved when I change to Exchange online mode. I think exchange online mode is not a permanent solution. Do you have any idea to fix this problem by running exchange cache mode? <br />
<br />
Thanks,<br />
Chanrith
</div>
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Hi there, 

There are many users outlook 2013 complain about repeatedly password prompts after migrated to exchange 2016. It must be a bug of outlook 2013, and it has resolved when I change to Exchange online mode. I think exchange online mode is not a permanent solution. Do you have any idea to fix this problem by running exchange cache mode? 

Thanks,
Chanrith

outlook 2013 repeatedly prompts password after migrated to Exchange 2016

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

Exchange

Microsoft Outlook is a personal information manager from Microsoft, available as a part of the Microsoft Office suite. Although often used mainly as an email application, it also includes a calendar, task manager, contact manager, note-taker, journal, and web browser.