Parental monitoring of digital media use evolves throughout childhood and adolescence and become increasingly important when autonomy seeking on social technologies emerges during early adolescence. We investigate a survey cohort of 248 US parents of early adolescents and their parental media monitoring behaviors (i.e., restrictive, active, deference), the family context (i.e., closeness and parent technoference), and perceptions of child’s problematic internet use. Using an explanatory mixed methods approach, the results of this study reveal that restrictive parental monitoring of adolescents’ digital media use is positively associated with child’s problematic internet use. However, active and deference monitoring are not associated with early adolescent problematic internet use and positively associated with family contexts. Familial closeness and technoference are consistent negative and positive correlates, respectively, of perceived problematic use among early adolescents. Qualitative interviews with a subset of 31 parents reveal while most parents report restrictive behaviors, multiple techniques (e.g., active, surveillant, and deference) are also leveraged when navigating their child’s online behaviors. Parents tended to converge on the same types and reasons for restrictive monitoring of media, whereas for other approaches the reasons behind their decision-making were quite divergent. The implication of this study is that parental media monitoring behaviors during early adolescence are rapidly evolving and not confined to a singular strategy, often related to prevention of or intervention on their child’s online behavior patterns. Understanding the family dynamics and parent involvement of adolescent’s digital media use remains critical in prevention of child’s problematic behaviors and promotion of positive online behaviors.