ISA 2006 site-to-site VPN with Cisco ASA 5510

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    I have NEVER worked on an ISA server and now I have been asked to configure a site-to-site IPSec VPN tunnel to a Cisco ASA5510.

    I am trying to create a LAB version to set the procedure first. I have installed VMware server on my PC at home and created a Win2K3 server with ISA 2006. Now as soon as I define some “Friendly” networks (my 2 offices public IP ranges) I am not able to even tracert to them (Destination host unreachable). All I have done is create the Network objects. I am not completely understanding the Network Rule structure… HELP! I am wanting to do some basic connectivity & rules tests FIRST (like RDP into the server from a “Friendly” network host). Then I think I will understand how to implement the instructions I already have… I hope!:-?

    Is there a REALLY basic How-To guide for getting this up and running?

    VM-only LAN (
    ISA 2006 internal NIC (
    ISA 2006 External NIC (
    Home LAN ( – GW:
    DD-WRT Router LAN (
    DD-WRT Router WAN (DHCP address from ISP)

    I have configured my DD-WRT Router with this Win2K3 server as the DMZ server (

    Thanks in advance,

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