Troubleshooting Outlook Anywhere issues

Resolving Outlook Anywhere issues can some time be very tedious. The best tool you can use to troubleshoot or test Outlook Anywhere is Microsoft’s own Remote Connectivity Analyzer available at

The interface is shown below:


To test Outlook Anywhere, you can select the Outlook Connectivity option selected above and click Next.

On the next page fill the text boxes as shown in the below screenshot.

Note:- If you have configured Autodiscover for Exchange, select the ‘Use Autodiscover to detect server settings‘ option to automatically detect your server or otherwise select ‘Manually specify server settings‘ to provide the settings manually. Also, when providing the settings manually make sure that under Exchange Server mention the internal hostname of the Exchange Server. Specify the type of Authentication configured either Basic or NTLM.



The connectivity analyzer will now perform a series of tests. There will be a slight difference in the tests if you have selected to detect the server using Autodiscover or manual settings. For manual settings the tests will be in the order:

  1. Resolve the external hostname of the Exchange Server in DNS
  2. Check and confirm that TCP port 443 is listening and open
  3. Check the validity of the SSL certificate
  4. Check the IIS configuration for client certificate authentication
  5. Check the configured authentication mechanism eg: Basic, NTLM, Negotiate
  6. Check valid ports 6001, 6002, 6004 etc..

In case of Autodiscover, the tests will be:

  1. Test the Autodiscover URL, https://url:443/Autodiscover/Autodiscover.xml
  2. Resolve the external hostname of the Exchange Server in DNS
  3. Check and confirm that TCP port 443 is listening and open
  4. Test the autodiscover URL, https://url:443/Autodiscover/Autodiscover.xml
  5. Resolve autodiscover.servername in DNS
  6. Check the presence of SRV record in DNS
  7. Check the presence of autodiscover cname record in DNS… etc..

If the server configurations are correct you will receive a notification that ‘The Outlook Connectivity test completed successfully.‘ else a failure message will be reported with the exact error.

One of the error I received recently is as shown below:


Troubleshooting the Exchange Server :

  • In the Exchange Server, check and confirm that RPC over HTTP Proxy feature is installed


  • Confirm the presence of a valid SSL certificate, and the name of the certificate is similar to the external hostname configured for Outlook Anywhere



  • Check the authentication configured for Outlook Anywhere and confirm its the same from Exchange Management Shell and in IIS
  • Check and confirm that the RPC Proxy server uses the valid ports for RPC over HTTP. From registry editor, navigate to  HKEY_LOCAL_MACHINE\SOFTWARE\MICROSOFT\RPC\RPCPROXY.

Make sure the data in the ValidPorts key is as follows :


The NETBIOS name and FQDN of the exchange server is required in this area.


  • Check and confirm that the authentication configured for the RPC virtual directory is IIS. This should be same as the authentication type configured for Outlook Anywhere



Once the above settings are verified, you can test the Outlook Anywhere connection either by configuring Outlook on an external machine or by using Remote Connectivity Analyzer.

For steps to test Outlook Anywhere on your machine make use of this link .

In order to test Outlook Anywhere configuration from powershell use the command “get-outlookanywhere | fl” etc…


Reference :


Enabling and configuring Outlook Anywhere

Outlook Anywhere is a feature by which you can access your company emails using Outlook  outside the LAN. It does not require VPN etc. Outlook Anywhere is also known in other terms like RPC over HTTP, Remote Exchange etc. This feature is available in Exchange version 2003 and later.

Outlook Anywhere is not enabled by default in the Exchange Server. Below are the steps to enable Outlook Anywhere on an Exchange 2010 Server.

  • Launch Exchange Management Console
  • Navigate to Server Configuration -> Client Access
  • Right Click on the Exchange Server on the middle pane and select Enable Outlook Anywhere


  •  Following are the settings you need to provide next for Outlook Anywhere to work successfully :


External host name :- This will be your Exchange server’s external host name which can be resolved over internet. Ideally this will be the domain name mentioned in your SSL certificate as well.

Authentication :- There are two types of Authentication mechanisms. They are :-

  1. Basic Authentication : It is generally used when the connecting computers are not the members of the domain. Also, your Exchange server will be directly connected to the internet, no proxy servers like ISA/TMG will be between your firewall and Exchange Server
  2. NTLM authentication : This type of authentication mechanism is used by domain members. You will have a proxy server in place in front of your Exchange server

SSL offloading :- Don’t select this option unless you’re sure that you have an SSL accelerator that can handle SSL offloading. If you don’t have an SSL accelerator that can handle SSL offloading and you select this option, Outlook Anywhere won’t function correctly.

  • It will take around 15 minutes for Outlook Anywhere to get enabled. Once enabled, you will notice application logs with event id 3008 in the Exchange Server

Client side configurations :

  • From Control Panel, navigate to Mail
  • Add a new Exchange account
  • Specify the internal hostname of the Exchange Server in the Server section and the logon name/alias in the User Name section


  • When the mentioned fields are filled, the More Settings tab will be enabled. Click on the same and navigate to Connection settings -> Enable Exchange Proxy Settings under Outlook Anywhere


  • Specify the external hostname of the Exchange Server in the below fields and select the configured authentication type



  •  Click on OK and finish the outlook configuration. Test mail flow and confirm that the outlook is working fine.