I think the bandit might end up catching you sneaking in the camp at random each time you do that or it happens after a certain number of successful sneaks at night.
You just need to sneak around till you bump into jester 2 times then you can get stuff going. To go further go to the track at night and look around you will eavesdrop on scar talking. Then go back to the camp at night and talk to jester about it. When you exhaust all of the dialogue options with jester you should be able to begin infiltration the next day.