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Have you sent the machine a Wake on Lan request? Does that machine have Wake on Lan capability, and is it enabled within the BIOS? Have you performed a successful Asset Scan against the machine? Are you blocking UDP 9?
Yes, and Yes
What is UDP 9?
The funny thing here is that it works one time, and if I try again it fails.
In order to successfully utilize the wake on lan feature, port UDP9 needs to be open on the target machine, and a successful asset scan will need to have been performed on said machine. The asset scan allows the NetChk Protect console to obtain the necessary hardware information from the target machine.