In his final years, Josiah Royce worked to develop his theories of community and interpretation in practical directions. In particular, he developed an account of insurance as a special community of interpretation, and proposed the creation of an international board of insurance as a deterrent for war. Rather than evaluating Royce’s policy recommendations, this paper explores how his conception of insurance clarifies his account of interpretation. For Royce, insurance provides the best model for communal interpretation thus far because an insurer seeks to prevent loss in the face of risky action, in addition to adjudicating between competing claims. This paper concludes with some reflections on how the problem of moral hazard can inform a Roycean conception of philosophy.