Exchange mailboxes not connecting through VPN after new server install

Posted on 2009-12-30
Last Modified: 2012-05-08
We installed a new Exchange 2007 box on Server 2008 into an SBS2003 enviroment and all appears working fine now except remote users that used to connect Outlook through VPN. All the internal users mailboxes appear to have updated fine but any user that connected through VPN will not connect. It just keeps showing trying to connect.
Is there anything i need to do ?

Question by:Netexperts
    LVL 3

    Expert Comment

    How is your VPN configured?
    How was the Exchange previously configured? On the SBS Server?
    is ISA on SBS and is this where the VPN comes in?
    Ensure ISA isn't blocking VPN to Exchange or another FW?

    Section 5 may be applicable?
    LVL 1

    Author Comment

    There's no ISA and VPN was and still is connecting via the old SBS2003 box. Exchange was on the SBS box and is still there but all mailboxes now moved over to the new server
    LVL 4

    Accepted Solution


    by design, if a users mailbox has been moved from Exchange 03 to another Exchange 03/07 server, as long as the Exchange 03 server is still online, when Outlook attempts to contact the last Exchange server (03) that it remembers, so long as the original Exchange server is still online and functional, it will either deliver the mail if the users mailbox (assuming the mailbox resides on this server) or Exchange will hand off the request to the secondary Exchange server in your environment.

    i'm wondering if there may be a hiccup in this process while attempting to do so over a VPN connection.

    another way around this is to start your VPN connection, ensure you can ping your new exchange server (you may need to use the FQDN), and then manually reconfigure the server settings within MS Outlook to point to the new server.

    If you're unable to ping your Exchange 07 box, or any other internal resources for that matter, then you have a routing issue, which will need to be corrected before you get MS Outlook working over a VPN connection.

    One last thing..  if you're using Exchange 07 or even Exchange 03 for that matter, you can set up RPC over HTTP/S (for Exchange 03) or you can set up Outlook Anywhere (for Exchange 07), which allows your MS Outlook client to send/receive email over HTTP/S.  personally, I prefer this method over VPN.  

    here's a good article on setting up Outlook Anywhere on Exchange 07:

    here's another article on setting up RPC over HTTP/S:

    hope that helps!  
    LVL 1

    Author Closing Comment

    It wasn't the answer to the question but after getting RPC over HTTP working it seemed a better idea.


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