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Due to security concern, by default you are not able to ping (ICMP protocol) a Windows Server 2008 machine. At first you could think there is a problem with your network but actually it’s disabled. To enabled ping reply from Windows Server 2008, go to 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 (picture below).
After that the check icon will turn green, representing that the rule is actually enabled:
For Windows Server 2008 Core (but even for normal Windows Server 2008) which does not have any UI, you can enable this rule from the command prompt (with elevated privileges):
netsh firewall set icmpsetting 8
To disable it type:
netsh firewall set icmpsetting 8 disable
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