Due to security concern, by default you are not able to Ping a Windows Server 2008 machine. At first I though there is a problem with my network but actually it’s disabled. To enabled Ping reply from Windows Server 2008, goto Window Firewall with Advance Settings from Administrator Tools menu.

Look inside Inbound Rules, scroll down to File and Printer Sharing, right click and enable this rule. (pic below)

After that the check icon will turn green

For Windows Server Core which does not have any UI, you can enable this rule from the command prompt.

netsh firewall set icmpsetting 8

To disable it type

netsh firewall set icmpsetting 8 disable