In recent years, increased attention has been paid to mental health struggles among students, and a range of interventions have been proposed to improve student retention and learning through "trauma-engaged pedagogy" and "cultures of caring." Drawing on the insights of affect theory, we argue that such a focus, although possibly helpful, ignores the role of alienation as a factor in student struggles. We further argue that assignment design is an overlooked and crucial site of student alienation, arguing that culturally relevant or politically inspiring readings and curricula will do little to ensure student engagement if assignments are arbitrary, artificial, and appear as simulacra of academic writing rather than as real sites of intellectual engagement. Drawing on our many years of experience as composition teachers at a community college as well as the work of colleagues and scholars and traditions of progressive pedagogy, we then suggest some criteria for assignments that foster engagement, offer lists of examples of such assignments, and outline a few of them in detail.