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Exchange Server 2013 Outlook Anywhere issue

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I am working on an issue with Outlook Anywhere in Exchange 2013 where external users cannot connect. This is a new server co-existing with an Exchange 2010 server that will soon be decommissioned.

When I run an Outlook Connectivity test on testexchangeconnectivity.com I get the following error. I am not seeing anything in the application or system logs. I already applied CU 6 (which was released today) and am seeing the same results. Port 443 is exposed directly to the web (no TMG, load balancer, proxy server, or SSL accelerator). Any help would be greatly appreciated! 


Attempting to ping RPC proxy <external Exchange URL>.
RPC Proxy can't be pinged.

Additional Details

An unexpected network-level exception was encountered. Exception details:
Message: The remote server returned an error: (500) Internal Server Error.
Type: Microsoft.Exchange.Tools.ExRca.Extensions.MapiTransportException
Stack trace:
at Microsoft.Exchange.Tools.ExRca.Extensions.MapiRpcTestClient.PingProtocolProxy(String endpointIdentifier)
at Microsoft.Exchange.Tools.ExRca.Tests.MapiPingProxyTest.PerformTestReally()
Exception details:
Message: The remote server returned an error: (500) Internal Server Error.
Type: System.Net.WebException
Stack trace:
at System.Net.HttpWebRequest.GetResponse()
at RpcPingLib.RpcPing.PingProxy(String internalServerFqdn, String endpoint)
at Microsoft.Exchange.Tools.ExRca.Extensions.MapiRpcTestClient.PingProtocolProxy(String endpointIdentifier)
Elapsed Time: 290 ms.

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