To live in human community is, in part, to owe debts to others and to be owed in return. How should we evaluate, normatively, the varied forms, practices, institutions, and relationships of debt? Which should be constrained and which accepted or encouraged? These questions have far-reaching implications given the pervasiveness of debt within human experience. This paper brings the resources of the capabilities approach developed by Amartya Sen and Martha Nussbaum to bear on normative assessments of debt. Our thesis is that the theoretical resources provided by this approach can help philosophers to examine the wide range of costs and benefits afforded by actual debts. We examine six contemporary examples of debt, arguing that the capabilities approach offers a nuanced and holistic framework for evaluating each. The framework is nuanced in that it provides resources for conducting fine-grained analyses of different cases and related policy proposals. It is holistic in that it takes into account more than a narrow range of either positive or negative considerations, instead encompassing the wide array of debt’s bodily, cognitive, and social impacts upon individuals.