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Troubleshoot Outlook Connectivity issues in Exchange 2013

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In earlier versions of exchange prior to Exchange 2013 troubleshooting outlook connectivity issues should be classified into categories according to the versions of exchange type of connections that we have configured in our environment.

Now lets see a small summary of Outlook connections from Exchange 2007:

1) In Exchange 2007 though the other  client connections was handled by Client Access server but still the MAPI connections were established directly to the mailbox server. 

2) In Exchange 2010 all the client connections including RPC went through the Client Access Server since the new service RPC client access service was introduced .

3) From Exchange 2013 we do not have the direct RPC over TCP connections at all and all connections should come only through RPC over HTTPS (Outlook Anywhere) or MAPI over HTTP if we have Exchange 2013 SP1 with outlook 2013 SP1 and MAPI over HTTP enabled.

I have collected few steps which will be useful if we come across these kind of scenarios in our environment :

Below are the things that can be checked during troubleshooting outlook connectivity issues in Exchange 2013:

1) Check if you have MAPI over HTTP or RPC over HTTP enabled in your organization.

If you have MAPI enabled then please run the command Get-MapiVirtualDirectory and check the MAPI internal and external URL:

https://exchangequery.files.wordpress.com/2015/05/mapi1.png?w=600

Now run the command to check if MAPI HTTP is enabled. By default it will be disabled and we need to enable them.

https://exchangequery.files.wordpress.com/2015/05/mapi2.png?w=600

 

Now lets look into troubleshooting Outlook connectivity issues in both the scenarios:

Telnet from the affected Workstation to your Outlook Anywhere external URL and ensure that the Outlook Anywhere URL is accessible on port 443.

Below is an example:

https://exchangequery.files.wordpress.com/2015/05/telnet.png?w=600

 

https://exchangequery.files.wordpress.com/2015/05/telnet1.png?w=891&h=215

 

Check the Outlook Anywhere authentication settings. By default it should be NTLM or it can be NTLM & Basic Authentication settings:

Get-OutlookAnywhere | fl Externalclientauthenticationmethod,internalclientauthenticationmethod

https://exchangequery.files.wordpress.com/2015/05/oa11.png?w=891&h=86

If Outlook Anywhere is not accessible from a particular network or site then most likely the issue could be on their network side. Probably you can check if Outlook Anywhere URL is reachable from their side. Ping the Outlook Anywhere URL from any of the affected workstations and see the results.

Also you can check if there are any recent changes in their network on their proxy servers.

If the affected site is routing their internet connections through the proxy site then you can test the connectivity by excluding your Outlook Anywhere URL in the proxy exclusions as below:

https://exchangequery.files.wordpress.com/2015/05/proxy.png?w=600

By doing this it will provide a direct connectivity to your site. Most likely these kind of issues might occur due to proxy connections. 

If its happening only for a single or few sets of users possibly check the MAPIBlockOutlookRpcHttp settings for that affected user by running the below command:

Get-CASMailbox mailboxname | fl MAPIBlockOutlookRpcHttp

https://exchangequery.files.wordpress.com/2015/05/mapi112.png?w=600

So this value should be set to false for the Outlook Anywhere to work. If this value is set to true then you have to set this value to false.

Ensure that the outlook anywhere hostnames are correct and they are added in your public certificates.

You can use the below command to check the host names:

get-outlookanywhere |fl *hostname

https://exchangequery.files.wordpress.com/2015/05/hs.png?w=600

If its for all users you can run outlookrpcselftestprobe on the affected mailbox server by running the below command:

Test-OutlookConnectivity -ProbeIdentity "OutlookRpcSelfTestProbe"

Check if the RPC can connect to store’s port by using RPC ping utility test by running the below command:

RpcPing –t ncacn_http –s ExchangeMBXServer -o RpcProxy=RpcProxyServer -P “user,domain,password” -I “user,domain,password” -H 1 –F 3 –a connect –u 10 –v 3 –e 6001

If it returns as following: Completed 1 calls in 60 ms 16 T/S or 60.000 ms/T, it means the RPC Ping Utility test succeeds.

You can also use EXRCA and see the results.

https://testconnectivity.microsoft.com/

Steps to perform the EXRCA tests:

  1. On the ExRCA website, under Microsoft Office Outlook Connectivity Tests, select Outlook connectivity, and then select Next at the bottom of the page.
  2. Enter the required information on the next screen, including email address, domain and user name, and password.
  3. Choose whether to use Autodiscover to detect server settings or to manually specify server settings.
  4. Accept the disclaimer, enter the verification code, and then select Verify.
  5. Select Perform Test.

Though there are more factors that can block the outlook anywhere connections in Exchange 2013 above troubleshooting steps can be helpful in some cases.

Hope this article is helpful.