Exchange 2010 Outlook Anywhere Not Working

Posted on 2012-08-15
Last Modified: 2012-08-21
We have three Exchange 2010 SP2 multiple role servers (mailbox, HT, CAS) in our environment which we plan to migrate our users to from Exchange 2007. Two of the servers are in one site and one is in another site. There is a CAS Array which points to an internal Kemp load balancer. We also have an external load balance at Rackspace pointing the Exchange 2010 servers. The purpose of the external load balancer is to point Internet traffic to the Exchange 2010 server in the other site in case of a disaster. Our Exchange 2007 environment consists of a Mailbox, CAS\HT, and an HT server.

OWA and Activesync in 2010 work fine but Outlook Anywhere does not work. Outlook Anywhere works in Exchange 2007. When Exchange 2010 users attempt to log in via Outlook Anywhere over the Internet they cannot. They keep getting prompted for their credentials which are never accepted. I have tried disabling Outlook Anywhere in Exchange 2007. I tried using NTLM authentication on the Exchange 2010 server and on my Outlook 2010 client. We are using a SAN certificate and all of the required names are on it. My test from gave me an "RPC Proxy Can't Be Pinged" error. Everyone is using either Outlook 2007 or Outlook 2010 as their client. I appreciate any assistance.
Question by:william_benson
    LVL 4

    Expert Comment

    by:Naushad shaikh
    Is your exchange 2007 is belong to other forest.If not is this prolebm is happing with migrated user only and outlook anywhere is working for exchange 2010 users?
    LVL 1

    Author Comment


    Exchange 2007 is in the same forest and the same Exchange organization as Exchange 2010. Only users migrated to Exchange 2010 have this issue. Exchange 2007 users can access their mail via Outlook Anywhere. The external hostname for Outlook Anywhere and the external autodiscover A record point to the Exchange 2007 CAS server right now. When I point the external hostname for Outlook Anywhere and the external autodiscover A record to Exchange 2010 neither Exchange 2007 nor Exchange 2010 users can use Outlook Anywhere.
    LVL 1

    Accepted Solution

    I fixed the problem myself. I mistakenly configured redirection on the RPC virtual directories of the Exchange 2010 servers. Once I removed that Outlook Anywhere worked fine in the 2010 environment.
    LVL 1

    Author Closing Comment

    I discovered the configuration error and corrected it, then I successfully tested Outlook Anywhere from a PC outside the network.

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