This chapter considers parental monitoring behaviors through the lens of Communication Privacy Management theory (CPM; Petronio, 2002). This chapter details the personal, relational, and cultural factors that guide changes in family privacy boundaries during adolescence, drawing parallels with other prominent theories of social development. Youth can interpret both overt (parental solicitation and control) and covert (“snooping”) monitoring as invasive of privacy; these subjective invasion perceptions are intricately associated with adolescent’s attempts to manage their personal information and maintain desired levels of privacy, but prior research is inconsistent regarding the presence, directionality, and valence of effects. Cultural factors can potentially explain this heterogeneity, including independent versus interdependent orientations toward self-construal, horizontal versus vertical orientations toward privacy control, and power distance in family relationships. Future research should examine parental motivations for intrusive monitoring, the accuracy of youth reports about such practices, and how families should handle information uncovered through parental invasions.