Configure Outlook Anywhere For Outlook 2016 Using Group Policy

In this blog post, I’ll show you to setup Outlook Anywhere using Group Policy on Windows 10 Clients with Outlook 2016 Installed.

You might want to use GPO to enable Outlook Anywhere If you didn’t or don’t want to enable it using Exchange Global Settings and the Set-Outlookprovider cmdlet.

Outlook 2010 and 2013 Outlook Anywhere

Before the release of Outlook 2016, Outlook Anywhere settings were available from the Outlook Account settings as seen below.

And after clicking on Exchange Proxy Settings… we get the Outlook Anywhere settings

Outlook 2016 Outlook Anywhere

Below, I have Outlook 2016 Account Settings and as you can see there Isn’t a connection tab to configure Outlook Anywhere.

The reason behind this change Is because Exchange Server 2013, 2016 and Exchange Online use https by default to communicate with exchange and the entire process relays on Autodiscover to configure clients.

In most cases, it works, however, If you have a mixed environment with Exchange 2010 and 2013 and above you might need to use GPO to configure Outlook Anywhere.

Group Policy Setup

To configure Outlook Anywhere using Group Policy you will need to Install Office 365 Administrative Tools, please visit the link below for step by step guide.

If you have Office 365 Administrative Tools Installed, Create and use existing GPO and go to:

User Settings -> Administrative Templates

Microsoft Outlook 2016 -> Exchange

Below you can see all the Outlook Anywhere and Exchange Settings, in this post I’ll focus on 2 options

Connection Flags and Authentication Settings

In my case I’m will enable all the Outlook anywhere settings and set Authentication to NTLM

Below, you can read about where each flag does

  • Flag 1: Enables the ‘Connect to Microsoft Exchange using HTTP checkbox’ on the Connection tab.
  • The following flags configure options in the Microsoft Exchange Proxy Settings dialogue box:
  • Flag 2: Enables the ‘Connect using SSL only’ checkbox
  • Flag 3: Enables the ‘Only connect to proxy servers that have this principal name in their certificate’ checkbox
  • Flag 4: Enables the ‘On fast networks, connect using HTTP first, then connect using TCP/IP’ checkbox
  • Flag 5: Enables the ‘On slow networks, connect using HTTP first, then connect using TCP/IP’ checkbox

And the authentication settings below set to NTLM

Exchange Global Settings

You can also set the settings above using Exchange Server Powershell cmdlets however once done they will apply to all users.

My recommendation Is to use the group policy first and test that it works before using the cmdlet below:

Set-OutlookProvider EXPR -OutlookProviderFlags:ServerExclusiveConnect
Set-OutlookProvider EXCH -OutlookProviderFlags:ServerExclusiveConnect

To revert the settings run the two lines below

Set-OutlookProvider EXPR -OutlookProviderFlags:None
Set-OutlookProvider EXCH -OutlookProviderFlags:None