Dockless bike share systems present an opportunity to expand access to bike share in cities by lowering costs and geographic barriers, but they also create additional challenges in the areas of maintenance, parking, and right-of-way management. Most dockless providers are private, venture-capital funded entities, representing a significant departure from current public and non-profit approaches. In several cities, municipal authorities have encountered challenges in securing cooperation from these operators in areas such as data transparency. This raises a key question: To what extent can municipal authorities use contracts and governance to exchange use of the public rights of way for operating requirements that advance equity, accessibility, innovation, and other goals? Using case studies from other U.S. cities and drawing insights from the wider “smart mobility” literature, this research presents recommendations for regulating dockless bike share in cities and ties these approaches to the implementation of Nice Ride Minnesota’s dockless pilot. It also examines prominent challenges in coordination and implementation and highlights novel approaches with an eye towards the future of bike share in the Twin Cities region (Minneapolis and St. Paul, MN). It concludes that providers of shared mobility services should expect to be regulated in exchange for use of public rights of way, while city authorities should provide transparent and proactive regulation, maintain an environment of iteration, define their own metrics for success, place planning goals before innovation, and strive for regional collaboration.