This communication explores the unique challenge of contemporary urban problems and the technologies that vendors have to solve them. An acknowledged gap exists between widely referenced technologies that city managers utilize to optimize scheduled operations and those that reflect the capability of spontaneity in search of nuance–laden solutions to problems related to the reflexivity of entire systems. With regulation, the first issue type succumbs to rehearsed preparation whereas the second hinges on extemporaneous practice. One is susceptible to ready-made technology applications while the other requires systemic deconstruction and solution-seeking redesign. Research suggests that smart city vendors are expertly configured to address the former, but less adept at and even ill-configured to react to and address the latter. Departures from status quo responses to systemic problems depend on formalizing metrics that enable city monitoring and data collection to assess “smart investments”, regardless of the size of the intervention, and to anticipate the need for designs that preserve the individuality of urban settings as they undergo the transformation to become “smart”.