I am trying to start my server remotely with this:
ssh firstname.lastname@example.org /sbin/reboot
And keep getting this back
ssh: connect to host xxx.xx.xx.xx port 22: Operation timed out
Why can't I start my server?
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In order to connect to a host using SSH, you need the SSH service to be running in the target machine. That's the reason for the timeout.
What you need is to setup the server for Wake-on-LAN. That means that when the LAN adapter gets a certain signal, it will start the physical machine. For this, you usually have to follow certain steps:
Depending on the OS you're trying to connect to, you can Google a tutorial for setting up Wake on Lan (WoL) on your flavor of OS.