This paper unpacks how actors navigate the multiple organizational, interorganizational and industry contexts that are associated with system transformation programs for addressing wicked, societal problems. Because system transformation programs can only succeed when changes are implemented by multiple organizations, an increased understanding of integrating programs in multiple contexts is needed. We draw on a qualitative field study of an interorganizational program designed to help transform the Dutch healthcare system. We identified three practices of context navigation that actors used to integrate the program into multiple parent organizations and address emerging incongruencies among contexts. These are aligning contexts, prioritizing contexts, and adding contexts. Over time, these navigating practices promoted progress towards program objectives via multiple parallel collaborative paths. Our findings shed new light on the role of breakdowns and decoupled collaborative paths in programs oriented at contributing to system transformation.