This investigation examined process-level pathways to nonsuicidal self-injury (NSSI; e.g., self-cutting, -burning, -hitting) in 2 cohorts of suburban, upper-middle-class youths: a cross-sectional sample of 9th-12th graders (n = 1,036, 51.9% girls) on the West Coast and a longitudinal sample followed annually from the 6th through 12th grades (n = 245, 53.1% girls) on the East Coast. High rates of NSSI were found in both the cross-sectional (37.2%) and the longitudinal (26.1%) samples. Zero-inflated Poisson regression models estimated process-level pathways from perceived parental criticism to NSSI via youth-reported alienation toward parents. Pathways toward the initiation of NSSI were distinct from those accounting for its frequency. Parental criticism was associated with increased NSSI, and youth alienation toward parents emerged as a relevant process underlying this pathway, particularly for boys. The specificity of these pathways was explored by examining separate trajectories toward delinquent outcomes. The findings illustrate the prominence of NSSI among "privileged" youths, the salience of the caregiving environment in NSSI, the importance of parental alienation in explaining these relations, and the value of incorporating multiple systems in treatment approaches for adolescents who self-injure.