Many times Windows server takes very long time to come up after a reboot. One of the main reason is due to the Windows update installation. I have seen VMs taking 2 hours to come up after a reboot. If the number of installed patches is very high, the time it will take to come up will be also high. So it is advisable to wait and not to restart the VM through the VMware console.
If you see your VMs in these below states, please wait, wait and wait.
Even if the VM is blank / black like below…
Even if you find the shutdown / restart option (soft) is all grayed out. Hold your horses.
This is applicable for Windows 2003 server also. Patience is your solution.
If you restart without waiting, you will definitely crash the VM.