Hubway, the Boston region’s bike share system, launched in 2012 and like all mature bike share programs, by 2016 faced new challenges like looming maintenance costs, the need to better serve low-income communities, and impending end of its existing operating contract and title sponsorship. Foursquare ITP aided the City of Boston in navigating these challenges and developing a sustainable vision for Hubway’s future. Our team conducted a detailed market analysis to determine locations of greatest ridership demand and areas where public policy and equity indicate bike share need. We tested expansion scenarios using a dynamic ridership and revenue model that Foursquare ITP customized for Hubway’s demand characteristics and financial structure. The final constrained plan informed the system expansion and future vendor procurement and sponsorship contracts.