This stand-alone chapter explores narratives from Caribbean tertiary educators on group work in higher education. Qualitative analysis revealed three central findings. First, group work is affirmed as a powerful pedagogical tool, captured in the theme Enhanced Learning with subthemes Collaborative Learning, Collective Efforts, and Reciprocity. Second, outcomes are shaped by group size and diversity, reflected in subthemes such as Conflicts, Dissolution, Size, and Tribalism. Third, group work equips students with interpersonal skills for professional life, represented by the theme Social Facilitation, Loafing, and Dominance. Issues of Assessment encompassed product versus process and grading methods. Collectively, these themes reveal conditions under which group work thrives or falters.