This study explores how parental control technologies affect family relationships from the perspective of adolescents aged 16-17 in the UK. Through seven focus groups with participants from diverse socioeconomic and cultural backgrounds, we examine how young people experience and negotiate the use of monitoring technologies within their families. Drawing on theories of connective labor and technological affordances, we identify three main themes: family practices in utilizing parental controls, adolescents’ experiences of monitoring technologies, and young people’s reactions ranging from collaboration to subversion. Our findings suggest that the effectiveness and acceptability of these technologies largely depend on whether they are implemented through open communication and support adolescents’ growing need for autonomy. Location tracking apps were generally more accepted than digital monitoring tools, particularly when used reciprocally within families. Notably, while private school students reported the highest levels of parental control use, they were also more likely to describe using these technologies for self-regulation. Young people across all backgrounds emphasized the importance of trust and communication over technological solutions. These findings have important implications for the design of parental control technologies and family-centered approaches to online safety that balance protection with adolescent autonomy.