In November 2016, the Government of India banned the vast majority of the nation’s banknotes in a move referred to as ‘demonetization’, with the stated goals of fighting corruption, terrorism, and eventually expanding digital transactions. In this study of 200 shop-keepers in Mumbai and Bengaluru, we found that cash shortage increased digital payment adoption but that digital payments fell after new banknotes became available. Digital payment adoption depended on the nature and scope of transactions, type of product sold, as well as personal factors specific to business owners such as comfort and familiarity with other digital technologies and online transactions. Using theoretical work on market and information behavior, we examined environmental pushes for technology adoption against prevalent transactional practices, trust, and control. We propose that the move toward digital payments must be framed within a larger undertaking of technology-driven modernity that drives these initiatives, rather than just the efficiency or productivity gains digital payments present.