What drives collaborating participants to leave collaborative arrangements? Collaboration is a dynamic and emergent process rather than a static condition. Previous studies focus on collaboration’s emergence and performance; few empirical studies examine why participants stop collaborating. We address this question by studying how the history and structure of the Illinois enterprise zone program relate to local governments’ renewing enterprise zone arrangements. We formulate hypotheses and provide empirical analysis at both the collaboration and individual participant levels to understand what relates to dropout. Using probit models, we provide evidence that participants of collaboration are less likely to drop out if the previous performance has been high when controlling for observable factors. Collaboration’s resource balance, stability, and participant similarity also relate to a lower likelihood of a participant’s dropping out of a collaboration. These findings shed light on the development of collaborative governance life cycle, particularly relating to later stages of collaboration.