Re: The stupidity is you
I said PHYSICAL access to the server sherlock or don't you know how to read.
This is pretty much the same as to access the OBDII port as you need to have 100% physical access to it (which involves breaking into the vehicle), the software to use it, and if the vehicles I've accessed the OBDII port on are anything to go off you also have to have the car on to use it so that would involve hot wiring it. At this point unless you stole the owners keys you have done some physical damage to the vehicle that would make the person suspect something.
So at this point for your plugging in the laptop to be similar that would also assume you broke into the server room, broke/reset the login passwords via some method, and at that point yes you would have access to the CEO's e-mail. But at that point seeing your entry will be detected why not just take the server, and run like you already will have the car on so just go.
Biting the hand that feeds IT
