The purpose of the present study was to investigate the contribution of the process of becoming less religious (BLR), compared with that of the dropout process, to youths’ well-being. The study focused on high school dropouts from Ultraorthodox Jewish communities, where dropout is accompanied by various social repercussions. On the basis of the conservation of resources theory, the study also focused on the loss of social resources—that is, sense of community, involvement and representation in the peer group, societal conditional positive regard (SCPR) and societal conditional negative regard (SCNR)—with respect to BLR and to dropout. The study, conducted in Israel among Ultraorthodox Jewish males, included 261 participants, ages 14 through 21 years (M = 17, SD = 1.17). A mediation analysis indicated a significant negative direct and indirect relationship via SCNR between BLR and subjective well-being. Becoming less religious was also correlated with low levels of the following social resources: sense of community and involvement and representation in the peer group. However, only a significant negative indirect effect of dropout stages on well-being via SCNR was observed. Dropouts reported higher levels of SCPR and SCNR than youth from the other groups, but there was no correlation with the other social resources. Findings highlight BLR as a greater risk factor for religious dropouts’ well-being, and for loss of social resources, than the dropout process. Implications for promoting positive well-being are discussed.