Studies have demonstrated parent involvement as an important predictor of academic achievement, social emotional skill development, and overall psychological adjustment. Much of the previous work on parent involvement has focused on mother involvement, leaving the role of father involvement in adolescents’ adjustment understudied. Further, this study was conducted during the COVID-19 global pandemic, which makes it unique in that some parents and adolescents were likely spending a significant amount of time with one another during the stay-at-home orders. Adolescents’ perspectives are important as they are a critical part of the family and at a critical transitional stage in which they are becoming independent and making decisions about their future. The goal of this study was to identify whether there are differences in the rates of involvement among mothers and fathers, if involvement is associated with adolescents’ school and wellbeing outcomes, and whether mother vs. father involvement has differential implications for adolescents’ outcomes. The second goal of the study was to determine if contextual factors (e.g., parent relationship quality, teacher-adolescent relationships, community belonging, social support) moderate the associations between parent involvement and adolescent adjustment. Adolescents (N = 116: mean age = 13.2) reported on their perceived rates of mother and father involvement, and their academic and socioemotional adjustment. Findings demonstrated significant differences in the levels of mother and father involvement, such that mothers were found to have higher rates of involvement than fathers. Although there were differences in the rates of parent involvement among mothers and fathers, the implications of their involvement were similar for adolescents’ outcomes. Parent-adolescent relationship quality significantly moderated the association between parenting involvement, both mother and father involvement, and adolescents’ socioemotional skills. In a similar vein, community belonging was found to moderate the associations between parent involvement and adolescent academic achievement (e.g., grades). Herein, while parent involvement generally plays a positive role in adolescent outcomes, other contexts, and the social capital gained within them, can reinforce, these contributions to adolescents’ academic and socioemotional adjustment.