In which cases my management doesn't care if I deviate from procedures and rules
The ones where it saves them money & you get away with it, ie. where no one in authority or the public reports it & embarrasses them.
and in which ones they will send me to jail?
The ones when you are caught & management is publicly embarrassed & does not support the pilot in question, coupled with an over zealous regulatory authority, goaded on by politicians, the competition and, to a lessor extent, vocal members of the public.
It is never wise to step outside the rules & procedures to help the company or fare paying public out. They never really appreciate it in the longer term & will drop you like a sack of hot potatoes when the mud starts flying.
It also leads to what is called 'normalised deviance' which is a whole other can of worms, that has been at least partially responsible for a number of accidents over the years.