Can't connect through WAN interface in VMWare Workstation 8

[MadsRC]

I'm currently setting up a lap in VMWare that consists of:
pfSense 2.0.3
Windows Server 2008
Windows 7

pfSense is only used as perimeter firewall and dns forwarder. The Windows Server runs DNS, DHCP & AD DC. Windows 7 is a test client.

In VMWare my networks are:
VMNet8: NAT with DHCP (Used for the WAN in pfSense
VMNet1: Host-Only no DHCP (Used for LAN in pfSense)

Now, the test machine and the Windows Server both can talk to each other and the firewall on VMNet1 and can also connect out through the firewall, through VMNet8 and onto the internet.

I've then created a NAT rule to map all traffic to 192.168.153.130 (The WAN IP on VMNet8) to 10.0.0.5 (The Windows Server running apache on the LAN) on port 80.

But if I change the test machine to run on VMNet1 (So that it is outside of the LAN) and tries to connect to 192.168.153.130 (Test machines ip is 192.168.153.131 so their on the same subnet) it times out.

Then I found that the WAN interface was set to block RFC1918 addresses, so I disabled that, but alas, still doesn't work…

Am I doing something entirely wrong? If you need screenies I'll be happy to supply them :)

[jimp]

Lots of things to check here:
http://doc.pfsense.org/index.php/Port_Forward_Troubleshooting

But first stop would be the firewall logs, then checking the state table to see if it shows up, some packet captures, etc… Only so many things to go wrong with a port forward.