Cyberbullying is a major health concern for today's youth and a pervasive stressor for adolescents and their families. This study offers qualitative insights into how parents perceive their children's technology use and engagement in cyberbullying based on gender. Eight focus groups were conducted with 48 parents of adolescents ages 10-17. Findings indicated parents perceived their children overuse technology and lack awareness of what cyberbullying is. Specific to gender, parents suggested their daughters use technology for social connection, and parents were more concerned about their daughter's technology use than their son's, which they believed was related to specific interests. In response to cyberbullying scenarios, parents encouraged females but not males to socialize with peers. This is the first qualitative study to obtain an in-depth understanding of the ways in which parents perceive and socialize their children in regard to technology use and cyberbullying scenarios. These results may help school systems, school psychologists, researchers, and parents gain awareness of the gender-stereotypical socialization process that unfolds in parental monitoring of technology use and cyberbullying situations. We conclude by offering suggestions for how school systems and personnel might intervene.