Outlook 2016 and Exchange 2010...

Bill Herde
Bill Herde used Ask the Experts™
Outlook 2016 and Exchange 2010...  

An issue came up when a user wants to use his personal laptop to connect for email.  
All other machines work fine because they are joined to the domain, and Outlook is set up for them the first time while connected to the LAN.  This PC of course can't do that.  

So, yes we know that Outlook 2016 no longer supports EAS, or has the settings available to manually set up RPC over HTTP proxy, and this needs to come from autodiscover.  Autodiscover is set up, and both the outlook connectivity and autodiscover tests pass on testconnectivity.microsoft.com.
BTW  older versions of outlook and most phones running Outlook can use autodiscover and set themselves up fine.

What I am not finding anywhere is WHAT INFORMATION IS NEEDED IN THE AUTODISCOVER XML file?  Surely if the requirement changed, there is a document somewhere with some insight on what to do.

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from where he is connecting his personnel laptop to exchange, from corporate network or from internet?

I assume from internet...

As long as you have setup internal and external URLs same, U should not any issues

have you also published mail.smtpdomain.com on internet and if it is setup as EWS external URL?

If yes, outlook should be able to automatically get configured once user enter user ID and password, no extra settings are required

what error you are getting? is it asking for passwords continuously ? or its not able to find exchange server ?

If its password not accepting, U might create standard user and assign him new mailbox and test if its working then
Could he connect a VPN to your server and then setup?
Would a VPN connection be a more secure access all of the time?
Bill HerdeOwner


Sorry for the delay, got called into a different crisis.

Internal is on a .loc domain, but the external domain name answers from inside. A DNS Cname entry sends them to the correct internal server.
mail.domain.com is published and webmail works from inside and out.
It is the never ending password request.  

Doing some more investigating, I found that a Outlook 2010 will no longer auto configure any more.  It used to, and I don't know how long it has been like this, but at least it simplifies the problem and makes a bit more sense.

Going into the basics today and just going to set it up all over again.
Bill HerdeOwner


This appears to have been broken ever since the last round of certificate renewals.  SAN certs stopped supporting .loc and .local names.  Web services and OAB still had different names.  also found that split DNS had been set up correctly for all but owa, which resolved another annoyance.  

Life is better now.  Thanks for the quick responses.

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