Squid in a virtual machine and VPN

  • I set up a virtual pc with VMware Workstation running pfSense which is set to work as a VPN client, that part seems to be working. Now I'd like to get traffic from a specific program on the host to go through VPN.

    Since Windows does not seem to have the capabilities to do that (it's all or nothing through VPN) I thought I'd have the program connect to a proxy server (Squid) in the virtual pc to force the traffic through there and then go through VPN.

    Unfortunately, I can't seem to get it working and I'm not sure why. The program in question gives time out errors when trying to connect and in Squid's log there's a bunch of "TCP_DENIED/403", "TCP_MISS_ABORTED/000" and "TCP_MISS/503" errors.

    It's probably a very simple thing, but I'm a newbie with both VPN and Squid and I don't see it. Could someone point me in the right direction? :)