10 pages., Article # 2FEA3, Via online journal., There are many potential advantages to collaborations between Extension and nonprofit organizations; however, it is unclear what factors contribute to a successful collaboration. We used an exploratory cross-comparative case study design to analyze four cases of highly successful Extension/nonprofit collaborations in one area in Florida. Using both deductive and inductive analysis processes, we identified several factors that contributed to the success of these partnerships: alignment of goals, longevity, informal adaptable partnering, relevant Extension agent background, delegation of tasks, marketability and fun, and relationship building. Exploration of these factors can inform future studies and has immediate, practical implications for Extension agents.