>>>"extremely careless" and "gross negligence"
>
>Not sure it's philosophical.
>
>If you are distracted and run a red light, that's extremely careless, even negligent.
>
>If you do it again the next day because it saved you so much time, but this time you mow down and kill three cyclists, then you're grossly negligent.
>
>Seems to me that "grossly" negligent means you knew your actions had the potential to cause great harm, but deliberately went ahead anyway. Usually not that easy to prove unless you're a repeat offender, fwiw.

You'd also have to show that harm did, in fact, result.
In the case of the server, that was never shown.
Carelessness, even negligence, when no one is hurt never gets before a judge.