I have an alarm setup to send me an email when a VM is starting up.
If I'm in the vSphere client and do a Restart Guest OS, the alarm works.
If I restart the OS via Remote Desktop, the alarm doesn't work.
The alert is created in the VM settings. This is at the level of the virtualization environment. When working remotely and reboot OS meaning that it is response from OS. The virtualization environment does not respond to this is normal.
Unless you can set an alarm related to VMware Tools being offline/online, you would be looking at Windows-specific methods rather than VMware-specific methods.