Thursday, November 09, 2006

Tip: Using Parallels for Mac with Check Point SecureClient on OS X

UPDATE: Installed the latest Parallels beta, 2.5 Beta 2 Build 3094, and in the limited testing I have done so far, CheckPoint can be connected to the Intranet before the VM is up. Once the VM is started, it just figures itself out. This is with Shared Networking in the VM, which has worked great.

Original Post
Since I am doing all my development work in Windows on a VM in Parallels for Mac, I need to use Check Point SecureClient VPN in either OS X or the VM to connect back to the corporate network. The majority of my day to day apps, Notes, TestTrack Pro, MS Office, Safari and Firefox, iChat and Adium, are running in OS X so for some of those I need the VPN connection available to OS X apps. So I can use that same VPN connection with my Parallels VM too right?

You can, but it turns out there is a little trick, at least I have found that to be the cause. The VM has to be running before SecureClient VPN is connected to your corporate network. Why would it matter? My guess is that SecureClient patches routing tables during its connection sequence, but doesn't do the same when new network interfaces come active, well at least the way Parallels does it. Also, didn't seem to matter in Parallels if I used Bridged Networking or Shared Networking (new in Parallels Build 2.2 Build 1970). Again just a guess, I am too lazy to dig that deep :-)