This study examined the contribution of mentor support to the following aspects of high-school dropouts’ lives: the personal (self-esteem, and the process of becoming less religious [BLR]), social (societal conditional positive and negative regard) and psychological (well-being and loneliness). The study, conducted among Ultraorthodox Jewish males, included 261 participants, aged 14 years to 21 years ( M = 17, SD = 1.17), who were at different stages in the dropout process. Findings indicated a significant difference in the contribution of mentor support. Among youths still in their yeshiva high schools, mentor support made only a minor contribution to the process of BLR; for youths in a program for dropouts, mentor support made a positive contribution to most aspects of their lives. However, among dropouts, mentor support contributed negatively to all aspects that were examined in the current study. Findings highlight the importance of further illuminating the role of mentor support and adapting it to youths’ needs.