After being exposed to several life-course transitions, and assuming that the major difficulties that characterize the period of early adolescence are over, the transition to high school should be easy. However, in reality for some students this transition is still significant and stressful. The difficulties stem from five characteristics of this process: an accumulation of difficulties; an overload of learning materials; unspoken threats regarding possible school dropout or negative evaluations of academic achievements; the obligation to make practical decisions regarding the future; and worries about the postschooling period. Studies on adjustment to high school establish only a limited body of knowledge, as many are short-term explorations without follow-up of possible long-term implications. Discussions of the teachers’ role, which is now even more significant than in secondary school, peers’ role, that is now less important, and parents’ role are provided. Following that, descriptions of interventions to support high school adjustment and to support the transition from high school to postschool life are presented and demonstrated