Encountering and/or engaging in risky online behavior is an inherent aspect of being an online user. In particular, youth are vulnerable to such risky behavior, making it important to know how they understand and think about this risk-taking behavior. Similarly, with parents being some of the first and most prominent influencers on youth’s online knowledge and behavior, it is important to know about parents’ understanding and how they attempt to protect/influence their children’s knowledge and behavior. In this qualitative study, we conducted surveys and semi-structured interviews with 40 youth/parent dyads with youth in 3rd-12th grades in the United States to understand more about how youth think about and engage in online risk and risk-taking behavior, and how their parents view and attempt to influence this knowledge. We found that youth of all ages have nuanced ideas about online risk—including viewing online risk as a source of resilience development, growth and learning—and that these ideas are often in contrast to how their parents view the same concept. Youth are more likely than their parents to view online risk as context-dependent and agentive, but are less likely than their parents to think about or understand the consequences of online risky behavior. We use these findings to discuss implications for parents, youth, education and tool providers, and future research.