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Exchange 2010 and Outlook 2016 - Autodiscover

I am currently receiving a lot of emails from people complaining about problems with Outlook 2016 in conjunction with Exchange 2010.

With Outlook 2016, a crucial function has apparently been removed for many: Exchange accounts can no longer be configured manually. To be honest, I didn't think that many people had configured their Exchange accounts manually.

Outlook always supports the current Exchange version, the two previous Exchange versions and the next two Exchange versions. In concrete terms, this means that Outlook 2016 supports Exchange 2016, Exchange 2013, Exchange 2010, the two future versions, but not Exchange 2007.

In an early Outlook 2016 preview, there was a registry key that could be set to activate RPCoverHTTP (better known as the Exchange 2010 Outlook Anywhere protocol). However, this is no longer necessary in the RTM version. In the screenshot you can see Outlook 2016 in connection with Exchange 2010, without any registry keys etc.

The reason why many people complain about connection problems has always been: No autodiscover configured!

As mentioned at the beginning, the manual configuration of Exchange accounts has been removed and PRF files are no longer supported. Here is a comparison between Outlook 2010 and Outlook 2016.

Outlook 2010:

Outlook 2016:

However, setting up Autodiscover accordingly is not rocket science either. Autodiscover automatically searches for its configuration; only the Exchange directories need to be configured in the IIS. The Autodiscover configuration is then created every 15 minutes.

Hier mal ein Bespiel für der die Verzeichnisse auf „outlook.frankysweb.de“ konfiguriert und Autodisover auf „autodiscover.frankysweb.de“

Set-OWAVirtualDirectory –Identity "OWA (default web site)" -ExternalURL "https://outlook.frankysweb.de/OWA" 
Set-OWAVirtualDirectory –Identity "OWA (default web site)" -InternalURL "https://outlook.frankysweb.de/OWA"

Set-OABVirtualDirectory –Identity "OAB (default web site)" -ExternalURL "https://outlook.frankysweb.de/OAB" 
Set-OABVirtualDirectory –Identity "OAB (default web site)" -InternalURL "https://outlook.frankysweb.de/OAB"

Set-ECPVirtualDirectory –Identity "ECP (default web site)" -ExternalURL "https://outlook.frankysweb.de/ECP" 
Set-ECPVirtualDirectory –Identity "ECP (default web site)" -InternalURL "https://outlook.frankysweb.de/ECP"

Set-WebServicesVirtualDirectory –Identity "EWS (default web site)" -ExternalUrl "https://outlook.frankysweb.de/ews/exchange.asmx"
Set-WebServicesVirtualDirectory –Identity "EWS (default web site)" -InternalUrl "https://outlook.frankysweb.de/ews/exchange.asmx"

Set-ActiveSyncVirtualDirectory –Identity "Microsoft-Server-ActiveSync (default web site)" -ExternalURL "https://outlook.frankysweb.de/Microsoft-Server-ActiveSync"
Set-ActiveSyncVirtualDirectory –Identity "Microsoft-Server-ActiveSync (default web site)" -InternalURL https://outlook.frankysweb.de/Microsoft-Server-ActiveSync

Set-ClientAccessServer -AutoDiscoverServiceInternalUri "https://autodiscover.frankysweb.de/Autodiscover/Autodiscover.xml"

The current configuration can be displayed with the following commands:

Get-ClientAccessServer | fl autodiscover*
Get-ActiveSyncVirtualDirectory | fl *url*
Get-OutlookAnywhere | fl *hostname
Get-WebServicesVirtualDirectory | fl *url*
Get-OwaVirtualDirectory | fl *url*
Get-OabVirtualDirectory | fl *url*

All that is needed now is a Certificate which contains the names „autodiscover.frankysweb.de“ und „outlook.frankysweb.de“ enthält und die DNS Einträge.

Most people will probably operate split brain DNS, i.e. the external domain, in this example frankysweb.de. is hosted by some provider. There, autodiscover.frankysweb.de and outlook.frankysweb.de are entered as subdomains, or HOST-A (depending on what the provider calls it). The HOST-A entries then contain the external IP address under which Exchange can be reached.

Do the same on the internal DNS, but with the internal IP address. Done. Don't forget to wait 15 minutes, this also works with Outlook 2016 and Exchange 2010.

Update 24.01.2017: A comprehensive white paper on how Autodiscover works and is configured can be found here:

Exchange 2016: Comprehensive white paper on Autodiscover

Update 31.03.2017:

Hier gibt es eine Konfigurationsanleitung inkl. Let’s Encrypt Zertifikaten:

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