Connecting to Exchange via VPN issues

Discussion in 'Parallels Desktop for Mac' started by kfordham281, Apr 21, 2007.

  1. kfordham281


    I'm hoping someone might be able to help me out a little here.

    I've got a Macbook 2Ghz with 2GB RAM and I'm running my boot camp partition through Parallels. When going into XP native (via boot camp) I can connect to my company network through the Cisco VPN client and using Outlook 2003 I can connect to my exchange mailbox just fine. However, when I run the boot camp partition through Parallels and connect to my company network with the Cisco VPN client, I'm unable to connect to my exchange mailbox. In the right hand side of Outlook it says "Trying to connect" and never connects to the mailbox.

    Anyone have any ideas? It's odd that it works through boot camp but running the boot camp partition through Parallels doesn't work. Thanks for any help!
  2. kfordham281


    Anyone, Bueller?
  3. wingdo

    wingdo Kilo Poster

    Since you give no details about your setup, I'm just going to throw a bunch of things to check out there and hope something sticks.

    Are you running the Cisco VPN client under Parallels or OS X? I've only run it under OS X and I have no issues connecting to Exchange.

    From within Windows under Parallels, can you ping the exchange server?

    What is its IP address? Perhaps the private subnet of your office is the same private subnet Parallels is giving XP.

    Try not using a NATted address in Parallels, click on Devices, Network Adapter, and then choose "Default Adapter" (and which ever is your active network connection, airport or ethernet). Then run the Cisco client.
  4. tomservo291


    Like the other response says, some things you can try:

    Get the OS X Cisco VPN Client (much less painful then the Windows Client. You can get a better front-end for it too such as the freeware app Shimo.) And give your Windows VM a NAT'd connection (such that all its traffic will go through OS X, and through your OS X VPN connection.)

    Or make sure your Windows VM connection is bridged when you are trying to use the Cisco VPN client.

    Some weirdness may be happening, since the Cisco VPN client disables all other network devices when it is connected. Once you have it connected, make sure you check all of your connectivity (VM to Host OS X, OS X to guest VM, OS X to outside network, VM to outside network (non-VPN) and VM to outside network (VPN).
  5. kfordham281


    Thanks wingdo.

    I was using the Windows VPN client while getting the "Trying to connect" message. I thought I had tried using the OS X VPN client (Cisco) but apparantly not because when I used the OS X version I was able to connect to Exchange in Parallels just fine.


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