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Checkpoint VPN Secure Remote Client working through ISA 2004?

ca99uk asked
Medium Priority
Last Modified: 2013-11-16

We have a SBS 2003 network with ISA 2004 installed. We have received some new software that needs to establish a VPN connection to an external network.

The VPN client is Checkpoint VPN 1 Secure Remote and needs to be installed on a couple of machines in the internal network. We are having some difficulty in getting the VPN to connect. We have contacted the software vendors however they are not very helpful just saying we should uninstall ISA, however this is not very practical.

If anyone can shed any light on getting this checkpoint VPN client to connect from our internal network to the remote site via the ISA server that would be great.

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I can understand the request to uninstall ISA hehe, it does tend to mess about with all VPN clients.

I would run a test to connect via secure remote while watching the firewall logs on the ISA box.  Look for any drops or errors, and then create rules to allow that traffic.

If it is getting through the ISA server, double check that you're upstream router/firewall is not blocking the traffic.

Basically, secure remote will negotiate a full VPN with the end point using IKE and IPSec, if both of these are allowed through your firewall/server, and of course the return traffic is allowed too, then it all should work fine.

Double check the logs on the ISA to see what it says with regards the VPN traffic and let us know what you find.


Hi Deimark,

thanks for the suggestion. We were going to look at that as a type of last resort :)

I am wondering if anyone has setup the checkpoint vpn client working with the ISA server?
Top Expert 2008
If you setup SecureClient to use Visitor Mode it will use port 443 for the vpn tunnel (https). When using Office Mode you can also specify that it shold use your default (internet explorer) proxy settings for connecting through the proxy server.

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