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Replacing Checkpoint SecureClient with IPSecuritas on Snow Leopard

So its that time again - another awesome Apple update to the best operating system in the world; for most, its a joyous time, one of new beginnings and wonderment.... for some, alas this is just an ideal as all there proprietary software comes crumbling down under a new kernel.

Friday was one of these momentous days, and yes, my world came crumbling down. For those who don't read my blog often I work remotely 85% of my working weeks as the company I work for are in another country so having a secure and speedy VPN is critical to actually getting paid and doing some work. After upgrading OSX 10.5 to Snow Leopard my Checkpoint SecureClient completely stopped working - this appears to be the plight of many users out in the interweb so I thought id write up this guide how to use IPSecuritas (as it rocks) which is infinitely better than the default checkpoint client (which sucks major ass!).

Why should I care about IPSecuritas?

This is simple - basically (as above) it rocks and has the following great features:

  • Its speedy.
  • Automatic connection recovery
  • Password persistance
  • Can talk to a bunch of different Firewall types... no more vendor tie-ins
  • Great OSX integration
  • Automatic connection upon login (instantly connected to VPN!)
  • Oh, did I mention its fast?

Removing Checkpoint SecureClient

OK, so now we've established that SecureClient is evil, lets remove it. Helpfully, checkpoint took the time to provde a shell script in the install directory to do just this. Open a Terminal window (Applications > Utilities > Terminal) and type the following:

# i'm not 100% sure on the names, as im writing this from memory, 
# but just have a poke around and you'll find what I mean.
timperrett$ cd /opt/C (press tab for auto-complete then return key)
timperrett$ open Uninstall.command

Type "yes" when prompted - the script will then go about removing all the various components. If your thinking of skipping this step, your free to, but remember than this installation is completely broken and wont ever run under Snow Leopard as it appears to be tied to the 9.x Kernel present in 10.5... so you might as well clean up and keep tidy.

Setting up IPSecuritas

If you havent already, download IPSecuritas from here - open the DMG and drag the application to your Applications directory. Once there, double click the application to load it for the first time - you'll need to enter your Administrator password then the application will install a daemon onto your system and configure itself. Once completed, take my advice and reboot your system - upon reboot you should see a new menu item that looks like a broken wire (below, dont worry about "XMPie", thats just what I decided to call my profile)...

Choose the "Open IPSecuritas" menu item - and up should spring the main GUI. You now need to configure a connection - this is what you will use to connect to your VPN endpoint (clue's in the name!). Making this connection is however a rather technical process for most users so im going to post screen shots of my configuration at every stage so that you can make something similar (yours may not be identical - it really depends on the setup implemented on the firewall; however, what I detail uses common place defaults).

So the two boxes in red are the important ones. For Remote IPSec Device you need to fill in the domain name or IP address of your firewall / vpn endpoint; this is organisation specific so i've removed mine. Secondly, Network address - this is the base IP range to which you want to connect to; again, organisation specific and yours will likely be different - if you don't know, check with an IT administrator.

These are standard security options needed to work with the checkpoint vpn - because I work long hours connected to the VPN, i've set it to timeout after 10 hours (essentially it never cuts me off and im in charge... sweet).

Again, this is standard checkpoint stuff so just copy the configurations as is - you don't need to know whats what.

So this is an interested panel - the two boxes ive marked in red need to be filled with your username for the VPN connection; you should have this already with that which you were using with the Checkpoint SecureClient system. In this example (and the checkpoint default) its using Hybrid RSA, but a lot of organisations use XAuth RSA etc that involve certificates etc... if you need this, just use the certificate manager and configure accordingly. I've also set it to remember my password so that I dont have to keep entering it - depending on your outlook, this is a good/bad thing. Personally, I think its a great timesaver!

Depending on your setup, you may want to configure specilized DNS servers - you might want this if you have servers that you wish you access with a UNC style such as:


Without specifying those DNS, your VPN will try to use external DNS and you just wont get what you want (or expect). I've removed mine for security reasons, but it should be fairly simple to figure out what you need to enter.

So this is the killer panel that confuses most people - you have some fairly finite control over the connection parameters - if your using Checkpoint VPN-1, just do as I have (unless your using another authorisation mechanism) and you should succeed!

Once you have all that, your good to go - just close the window, and click "Start" on the main IPSeceritas window then provided all went well you should get a green light next to the connection name - in my instance, i called the connection "office". If you are having issues, seek help from your IT administrator as it might be a configuration issue - with VPN's your client much EXACTLY match what the endpoint is configured to... any miss-match at all will result in failure; however if you wish to debug the issue yourself, bring up the connection log from the top bar menu and you'll be able to see exactly what is going on under the hood (if you need a boat load of wire information, set the logging level in preferences to DEBUG and then restart/reboot IPSecuritas)

Enjoy, and good luck.

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