Using literature and illustrations drawn from a pilot study, this article explores the theoretical and methodological challenges entailed in the study of student retention. We center the discussion around two important efforts to expand the theoretical base and scope for research in this area: Berger's (2000) concept of colleges and universities as optimizers of cultural capital and Bensimon's (2007) recent critique of the narrowness of the frames that predominate student retention research. By way of exploring these issues through a concrete example, the article presents an overview of processes and findings from a funded pilot study of institutional policies and practices surrounding student retention. This exploration--part essay, part research report--leads us ultimately to pose two central questions on which, we suggest, future research should build: "What are institutions doing to improve student retention?" and "How do institutions intervene in the workings of cultural capital in higher education?" (Contains 2 tables.)