If response comes back failed, and name is resolvable (or it was already just an IP address) and that IP address is on the same subnet as Mycroft, and Mycroft has a cached MAC address for the requested host, then generate a WoL/Magic Packet and ask the user "Shall I attempt to send a wake-on-LAN signal?" and if user affirms, then transmit.
Correlated feature: create a simple key/value text cache. At the end of every successful ping, lookup and cache the MAC address.
Possibly after sending WoL packet, offer to retry ping. Maybe at 20 seconds, 1 minute, 3 minutes, then give up (and issuing an utterance to that effect).
If response comes back failed, and name is resolvable (or it was already just an IP address) and that IP address is on the same subnet as Mycroft, and Mycroft has a cached MAC address for the requested host, then generate a WoL/Magic Packet and ask the user "Shall I attempt to send a wake-on-LAN signal?" and if user affirms, then transmit.
Correlated feature: create a simple key/value text cache. At the end of every successful ping, lookup and cache the MAC address.
Possibly after sending WoL packet, offer to retry ping. Maybe at 20 seconds, 1 minute, 3 minutes, then give up (and issuing an utterance to that effect).