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Our research aims to highlight and alleviate the complex tensions around online safety, privacy, and smartphone usage in families so that parents and teens can work together to better manage mobile privacy and security-related risks. We developed a mobile application ("app") for Community Oversight of Privacy and Security ("CO-oPS") and had parents and teens assess whether it would be applicable for use with their families. CO-oPS is an Android app that allows a group of users to co-monitor the apps installed on one another's devices and the privacy permissions granted to those apps. We conducted a study with 19 parent-teen (ages 13-17) pairs to understand how they currently managed mobile safety and app privacy within their family and then had them install, use, and evaluate the CO-oPS app. We found that both parents and teens gave little consideration to online safety and privacy before installing new apps or granting privacy permissions. When using CO-oPS, participants liked how the app increased transparency into one another's devices in a way that facilitated communication, but were less inclined to use features for in-app messaging or to hide apps from one another. Key themes related to power imbalances between parents and teens surfaced that made co-management challenging. Parents were more open to collaborative oversight than teens, who felt that it was not their place to monitor their parents, even though both often believed parents lacked the technological expertise to monitor themselves. Our study sheds light on why collaborative practices for managing online safety and privacy within families may be beneficial but also quite difficult to implement in practice. We provide recommendations for overcoming these challenges based on the insights gained from our study.