Enable ICMP echos in Server 2008
To enable ICMP replies in Windows Server 2008 you must allow ICMP packets through the windows Firewall
Goto -> Administrative tools
Click on 'Windows Firewall with Advanced Security'
Click on 'Inbound Rules'
Scroll down to find: 'File and Printer Sharing (Echo Request - ICMPv4-In)'
Right-click on this and choose 'Enable Rule'
Congrats, you can now ping the 2008 server.