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Outlook still pointing to old exchange server even after mailbox move

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  • Outlook still pointing to old exchange server even after mailbox move


    Well the lengthy title says it all. We had Exchange 2010 running on one server will all 3 roles installed and recently that server stated to act up so we moved exchange onto 2 new servers in a DAG.

    Because the old server (let’s call it oldA) is still being used, i need to move mailboxes to the new servers (let’s call these newB & newC) like a migration until everything is off of the oldA server and then I can decommission it. My external pointer and owa still pointing (for now) to oldA server.

    As i do these mailbox moves (5 so far), i have noticed that outlook is not picking up the new server automatically. Although in the certificate I have included and, along with their host names. I had to perform a repair for them to pick up the new servers.
    Is this because is not pointing to the right server or is this something i have to deal with? I read that outlook 2010 & 2007 should automatically pickup new exchange server names?

    In addition, i was thinking of putting in a 3rd server (let’s call this newD) and let it act like a traffic cop. Meaning i point to it and it in turn sends requests to the 2 new servers (newB & newC) in DAG? Will that work?

    What is the easiest method and will outlook automatically pickup new exchange servers in their profile (not looking forward to repairing 100 + outlook clients).

    Thanks for patience and your responses.
    Last edited by Sembee; 22nd July 2011, 12:02. Reason: Formatting Correction

  • #2
    Re: Outlook still pointing to old exchange server even after mailbox move

    The reason the mailboxes don't appear to be changing is because of the change to the architecture of Exchange.

    With Exchange 2010 clients (Outlook, OWA, ActiveSync etc) do not connect to the mailbox server, they connect to the CAS server. The mailbox doesn't belong to a server, it belongs to the ORG. Therefore because the CAS server is still available, the Outlook client continues to work.

    The DAG is purely for the database data. It has nothing to do with the client accessing the mailbox.

    The process that you have described at the end of your question is already in Exchange, and realistically if you are using a DAG you should have implemented it already. That is a CAS Array. This is effectively a virtual Exchange server that only exists in DNS. It can be pointed to a CAS server, a WNLB or a third party load balancer.

    Therefore you should setup the CAS array immediately. The CAS array host name should not resolve externally, it should be a unique name. The usual name is "outlook" - so outlook.domain.local. If the name resolves externally then it can cause a problem with Outlook Anywhere.
    The CAS array creation is documented on Technet.

    Unfortunately, there is no straight forward way to update the clients, which is why I implement a CAS array on all sites I install, even if it is just a single server deployment. It is far easier to use the CAS array from the start than trying to retrofit it.
    Autodiscover will not update the clients, which means you have two options.

    1. A new Outlook Profile.
    2. Repair the Outlook profile.

    The second option is the easiest and is quite easy to get the end users to do. Just ask them to click repair in Outlook.

    You could look at using something like PRF files for Outlook, or one of the MAPI profile configuration tools, but these have been largely dropped because of Autodiscover.

    Simon Butler
    Exchange MVP

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    Sembee is a registered trademark, used here with permission.


    • #3
      Re: Outlook still pointing to old exchange server even after mailbox move

      Thank you for your detailed explanation. I have implemented CAS array and am pointing all outlook clients to it. So far so good.

      I have noticed one thing though, when external clients connect using outlook anywhere, it keeps prompting them for a password which it won’t except. They have to keep entering it and finally it will accept it and will connect.

      Half of our users work from home so they're here in the office on Monday and the rest of the day from home. I have taken some of these remote users and repaired their outlook profile and now it reflects the new cas array name. It is these folks that are getting the popup for username and password which can get annoying for them. Like i said, it will eventually connect, but takes a long time.
      Any thoughts why?

      Thank you in advance.


      • #4
        Re: Outlook still pointing to old exchange server even after mailbox move

        Never mind i figured it out! The issue was 2 prong.

        First, outlook anywhere url was set to point to rather than so i made the necessary change there.

        Second, i came across this article which states "In XP you have to configuring the common name of the certification(the name after “Issue To”) after the “msstd:” in user’s profile. Otherwise, the Outlook will always repeatedly prompts for password. XP is not willing to look at next lines on a SAN certificate, but Windows vista/7 does. And we should use the command to set outlook provider as well: Set-OutlookProvider EXPR -CertPrincipalName:""msstd:yourdmoain" .

        Since most of these workstations are xp and they're experiencing issues and mine was windows 7 and never saw this issue during testing, explains it.
        By running the set-outlookprovider command, i was able to set the outlook anywhere provider to point to the right server.

        Thanks everyone for your assistance.