Drawing on the work of Patrick Saint-Jean, S.J., this article examines the contribution that “possibility thinking” makes to community-engaged learning at three Jesuit universities. The article considers ways in which possibility thinking intersects both Jesuit and secular perspectives on hope and imagination, and their relationship to anti-racist praxis. We then describe three institutional contexts at different stages of enacting community-engaged learning in introductory and upper-level English classes. The article concludes by offering three praxis-oriented directions for community-engaged learning educators to take up in their own institutional contexts: developing faculty capacity and awareness; fostering solidarity not charity; and encouraging reflection not reaction.