Plugin

[Hello World]

I think a chat message would suffice for >20 seconds in jail followed by 10 slaps or so if they go beyond 30seconds.
As previously mentioned it isn't possible on all maps, but also I think it requires a more generic function where you shouldn't have to pre plot each maps coordinates for jail.

Thus I'd propose just an anti camp plugin or zone plugin ( zone being how the map vmf decides on zones) that provides the above features