Amsterdam has historically been and continues to be a thriving “global city,” acting as a commercial and financial hub, and has made significant advances in digitizing, automatizing, and datafying urban life. Withdrawing from digital space would mean giving up on countless pleasures and conveniences afforded by communication and navigation devices. The research was conducted through expert interviews and focus groups in Amsterdam during 2015. The majority of focus group participants acknowledged the conveniences afforded by the smart city: be it the fast and easy finding of the next train connection through online apps or the convenience afforded by using digital calendars. The residents of a smart city are often referred to as the “users,” “end-users,” consumers or beneficiaries. Creating a democratic city livable for its citizens, questions beyond the labels of “convenience, efficiency, and security” need to be addressed through continued public debate.