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Exchange 2010 Outlook Anywhere cert error but only after successful login

Posted on 2012-03-13
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Last Modified: 2012-03-15
I have a new Exchange 2010 installation. I've purchased a UC/SAN certificate with a number of alternative names included to cover the FQDN of all CAS/HT servers as well as autodiscover and the standard recommended name.

I've installed the cert on our hardware loadbalancer and set up SSL offloading.

When I connect using Outlook 2010 and Outlook Anywhere, the autodiscover service works fast and perfectly sets up the account and then I can connect Outlook without incident.

However, 30-45 seconds after a successful login and without interrupting anything I get a security alert. It appears to reference the self-signed cert created in the installation of Exchange. I'm not sure what is triggering the need for the cert. The top of the error shows the FQDN of one of  my cas/ht servers which is included in my UC/SAN cert.

I'm pretty sure this something that is not being properly pointed to by my load balancer but I'm not sure what it is. I currently have ports 110, 143, 993,, 25, 587, 443 and 80 setup for load balancing.

What am I missing? Any help appreciated.
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Question by:hcca
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by:SMurphy11
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Have you also installed your purchased certificate on your CAS servers?  

In fact, you should have generated the request for your UC/SAN certificate in Exchange using either the EMC or the shell.

It sounds to me like it is not installed in Exchange or the services have not been assigned to that certificate.
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by:hcca
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I have not installed the cert on the CAS servers because I intended to do all SSL offloading, though I can do this if necessary.

I did generate the request from the EMC.

I just ran a test from https://www.testexchangeconnectivity.com/ and it reports that common name on the UC cert does not match the "msstd:domain.com" in the Outlook client. It says this causes  a failure of the SSL mutual authentication with the RPC proxy server.

Is this what is causing the error?
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by:SMurphy11
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Yes.. so, complete the request and assign the cert to the services in Exchange and you should be good to go.

Basically what is happening is the load balancer doesn't trust Exchange's self-signed cert.

Also, since you generated the request in Exchange, my guess is the load balancer doesn't have the private key that goes with that cert.   After you import it in Exchange and assign it, you can export it with the private key and add it to the load balancer.
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by:hcca
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The load balancer was configured with the private key for the cert. As I said, it is doing the SSL offloading without a problem for the Outlook Anywhere. It is sometime after that connection is established that the security alert comes up.
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SMurphy11 earned 500 total points
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I understand the SSL offloading.  Bottom line is Outlook Anywhere will not work with a self-signed certificate.

Complete the pending request in Exchange 2010 and install your third-party certificate there and assign it and everything should work as you expect.
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