The home-leaving transition of male adolescents in Israel, where most 18-year-olds leave home to perform a 3-year mandatory military service, was examined. Transfer of attachment functions from parents to peers across the transition and adjustment to the basic-training period were investigated. Adolescents ( N = 143) filled out questionnaires 3 months before conscription and 6 months later, following their basic training. Before conscription, participants were in the midst of the process of transfer, and attachment insecurity was associated, as expected, with less transfer. Contrary to expectation, high fear of closeness was associated with increased transfer of proximity seeking from parents to peers across the transition. This contributed to better adjustment, offsetting the negative effect of low hardiness. Anxiety over abandonment was negatively associated with adjustment, with low hardiness mediating part of this effect. Results are discussed in light of developmental changes in relationships with primary caregivers during the home-leaving transition.