The increasing popularity of the Internet and social media is creating new and unique challenges for parents and adolescents regarding the boundaries between parental control and adolescent autonomy in virtual spaces. Drawing on developmental psychology and Communication Privacy Management (CPM) theory, we conduct a qualitative study to examine the challenge between parental concern for adolescent online safety and teens' desire to independently regulate their own online experiences. Analysis of 12 parent–teen pairs revealed five distinct challenges: (a) increased teen autonomy and decreased parental control resulting from teens' direct and unmediated access to virtual spaces, (b) the shift in power to teens who are often more knowledgeable about online spaces and technology, (c) the use of physical boundaries by parents as a means to control virtual spaces, (d) an increase in indirect boundary control strategies such as covert monitoring, and (e) the blurring of lines in virtual spaces between parents' teens and teens' friends.