Institutional and societal changes that arise from digital technologies have been multifold, including the disruptive changes for contract workers. This study examines how Uber replaced existing norms and rules in the transportation industry, depriving drivers of their fundamental rights, including minimum wage and paid leave. The chapter reviews new forms of labor exploitation and how deregulation and information deprivation affect the material conditions of Uber drivers. The study draws on the author’s experiences working as a driver on UberX. Instead of calculating wages based on time during a customer’s ride, time is viewed as all active time on the platform. The exclusive access to information and the power of management algorithms enable Uber to exploit drivers in more sophisticated ways. New dispossession processes are negatively affecting workers’ material status and capacity for collective action. Yet, recent mobilization and street protests by Uber drivers provide a glimpse of hope and call attention to new forms of labor organization among contract workers.