It is often uncritically assumed that, when digital technologies are integrated into the operation of city functions, they inevitably contribute to sustainable urban development. Such a notion rests largely on the belief that Information and Communication Technology (ICT) solutions pave the way for more democratic forms of planning, and that ‘smart’ technological devices result in a range of environmental benefits, e.g., energy efficiency and the mitigation of global warming. Drawing on the scientific literature that deals with ‘smart cities’, we here elaborate on how both propositions fail to consider drawbacks that could be characterized as ‘wicked’, i.e., problems that lack simplistic solutions and straightforward planning responses, and which often come about as ‘management surprises’, as a byproduct of achieving sustainability. We here deal with problems related to public choice constraints, ‘non-choice default technologies’ and the costs of automation for human learning and resilience. To avoid undemocratic forms of planning and too strong a dependence on non-choice default technologies, e.g., smart phones, we recommend that planners and policy makers safeguard redundancy in public-choice options by maintaining a wide range of alternative choices, including analog ones. Resilience thinking could help planners deal more effectively with the ‘wickedness’ of an increasingly hyper-connected society.