This chapter employs an approach that integrates theoretical tools from core strands of transition scholarship to uncover the roots and chart the pathway of Vancouver's transition. It reveals the transferable lessons demonstrated by Vancouver's leadership, with a particular focus on innovative modes of governance and networks of actors. The chapter contributes to longitudinal analysis that begins to demonstrate whether sustainability strategies put in place over the last two decades have actually borne fruit. Long before the provincial government began employing legislative tools to trigger action on climate change, however, the City of Vancouver had developed and implemented a wide array of sustainability measures, public engagement strategies and long-range planning processes. Taken together, these efforts represent significant steps along the pathway to an urban sustainability transition. The chapter explores how these activities have unfolded over time and space, with the ultimate goal of revealing both the crucial ingredients of this transition and its ultimate transformative potential.