This chapter introduces the Caribbean Collaborative Action Network (CCAN) and situates it in relation to the evolving activities of community-engaged climate adaptation in Puerto Rico and the US Virgin Islands. Funded under the National Oceanic and Atmospheric Administration (NOAA) Climate Adaptation Partnerships (CAP), CCAN is a multi-pronged knowledge and action network that seeks to support community-based climate adaptation efforts in Puerto Rico and the US Virgin Islands (USVI). The chapter presents the goals of the NOAA CAP program to support community climate adaptation. It then considers critical social science perspectives on “resilience” and adaptation; the concepts of social infrastructuring and the co-production of knowledge; and offers a reflective analysis of the positioning of our own WPI-based research team as part of CCAN. This leads to the concept of creative climate collaborations.