MacBook running Parallels 7. Guest OS is Windows 7 with all patches and Office 2010 with all patches. This is running on a network with and Exchange server. While here, there are no issues. When working from home over VPN (using the Mac's built in Cisco VPN option), Outlook will stop connecting. At first I thought it was all VPN. The only thing that would fix it is a reboot. Today, this happened again. VPN on the Mac Host is working perfectly. Outlook for Mac connects to Exchange with no issue. On the Guest, I can connect to a network share, but Outlook can't find the server. I've tried to disconnect the network adapter from the VM and reconnect, but no luck. If I reboot the entire machine, it works again. So, Internet and VPN traffic is being passed from the Host to the Guest, but for some reason it's not allow Exchange traffic through. Now, it will work for some time, but will stop without any warning or other error, Outlook just stops connecting until everything is rebooted. Any help is greatly appreciated.