In January 2016, I co-organized a Jamaica cultural immersion and faculty development trip in which ten professors from two Southern California universities participated. Our objective during the week-long program was to explore opportunities for faculty to incorporate community immersion and engagement into existing international programs, and to help conceptualize new international study abroad programs featuring a community engagement component. A growing body of literature has demonstrated the importance of cultural immersion and community engagement experiences in advancing critical thinking and global competencies in students, but fewer papers have shifted the lens to faculty as they are first introduced to conditions similar to those of students studying abroad. This descriptive paper focuses on the Jamaica trip as a backdrop to discuss some of the challenges and opportunities for faculty leading community engaged study abroad programs.