“There’s an app for that” is perhaps the definitive rhetoric of our times. To understand how users navigate the trade-offs involved in using apps that support a variety of everyday activities, we conducted scenario-based semi-structured interviews (n = 25). Despite the technical and regulatory mechanisms that are supposedly meant to empower users to manage their privacy, we found that users express an overarching feeling of resignation regarding privacy matters. Because these apps provide convenience and other benefits, as one participant put it, “there is a very fine line” that marks the divide between feeling empowered in the use of technology and coping with the discomfort and creepiness arising from invasive app behavior. Participants consistently expressed being resigned to disclose data even as they accepted personal responsibility for their own privacy. We apply the findings to discuss the limits of empowerment as a design logic for privacy-oriented solutions.