Outlook 2016 Password Prompt Not Working

I have a user that has a Lenovo laptop with Windows 10 Pro and Outlook 2016 Home & Business.  Their office uses SBS 2011 with Exchange 2010 Standard.

I setup this laptop about 2 or 3 months ago, and since about two weeks the user cannot connect with Outlook when outside of the office.  For instance if the user is at home and they attempt to open outlook it asks for the password, but does not accept it.  The user account is not locked and I confirmed the password is correct by logging onto OWA without issue.  I also deleted all Credential Manager entries just in case.  I also created a new Outlook Profile.  I confirmed the Outlook account does not have Prompt for password under the Security tab.

So, the only way Outlook accepts her password and updates is if she invokes a VPN connection.  Once the VPN is up then she can successfully log onto to Outlook and work without issue.  I also believe the laptop is fully patched with the exception of the Creator's October update.
cmp119IT ManagerAsked:
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Olivier MARCHETTACitrix Support and Infrastructure EngineerCommented:
I am not an Exchange expert, but do you use the RPC over HTTPS (Outlook Anywhere) on the server ?

cmp119IT ManagerAuthor Commented:
I reviewed this article and I do not believe its was much help for my situation.  On their exchange 2010 server the only difference from the instructions is Outlook Anywhere uses Basic Authentication instead of NTLM Authentication.  I believe that is fine since the Outlook client Encrypts the data between Outlook and the exchange server.

Also the instructions are for Outlook 2010 and Outlook 2016.  The 2016 version Security Tab does not any settings for HTTP or proxy settings.  You can also see their is no Connections Tab anymore.

Outlook Encryption Settings
Olivier MARCHETTACitrix Support and Infrastructure EngineerCommented:
If you do not want to use a VPN you need to allow access to your Exchange server through your external firewall first.
Have you configured the port TCP 443 (HTTPS) forwarding from your external firewall to the Exchange server ?
Regarding Outlook 2016, the connection tab has been removed indeed, and you need to use the autodiscover configuration instead (or a GPO, or a registry key).
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cmp119IT ManagerAuthor Commented:
Yes port 443 is forwarding to the internal exchange server.  This has been working and as of two weeks ago has stopped.
Olivier MARCHETTACitrix Support and Infrastructure EngineerCommented:
I found this topic :


- would it be possible to create new outlook profile for this user and test ? (backup the old profile)
- can you try to enable NTLM security for the Outlook Anywhere authentication feature on your Exchange 2010 server ?

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cmp119IT ManagerAuthor Commented:
don't ask me why but the problem turned out to be adding an SRV record with the company that manages DNS for us.  Autodiscovery appears to be working now and no password prompts anymore.  Yes, please close this case.
Olivier MARCHETTACitrix Support and Infrastructure EngineerCommented:
closing the question
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