But after a year, Shekhtman wanted more privacy and moved to a trailer on a hill outside the settlement. Though Israel considers such trailer outposts illegal, Shekhtman's was hooked up to running water and electricity through Tapuach. The newcomer befriended other boys in the area, including some living even more austerely in tents on nearby hillsides. He spent the Sabbath with these boys and gave them rides in his car, once helping them move a tent.

Shekhtman's friends were part of the so-called hilltop youth, a loosely affiliated group of Jewish settlers in their teens and 20s who live away from their parents on the hilltops surrounding established settlements. Members of the group have perpetrated so-called "price tag" attacks, using firebombs and spray paint to damage Palestinian property in retribution for Palestinian violence, or as a way of lashing out against the Israeli military.