Parental involvement is an essential factor that influences a child’s learning, behavior, and every other aspect of life, including online interactions. While holding parents responsible for the consequences of children’s online actions and overall well-being, we often overlook the importance of and need for means that can effectively support parents in interacting and engaging in activities with their children. In the present study, we describe and evaluate a collaborative family game called “CyberFamily” to facilitate parent–child collaboration and leverage family communication, intending to increase cybersecurity awareness among children aged 9–12. We also present the results of two user studies: one conducted with four parent–child dyads to test the feasibility of the game and a second user study conducted with 11 parent–child dyads focusing on evaluating the usability of CyberFamily. Our findings yielded positive feedback and showed that a collaborative family game like CyberFamily can help parents engage with their children’s online activities, leading to discussions and the potential for collaborative learning for both groups. We suggest that future researchers and designers consider and provide an active, engaging role for parents when developing solutions to raise cybersecurity awareness among children, rather than just having parents monitor and control children’s online access and activities.