Existing empirical research suggests that human resource ofﬁcials, managers, and in-house counsel inﬂuence the meaning of antidiscrimination law by communicating an altered ideology of what civil rights laws mean that is coloured with managerial values. This article explores how insurance companies play a critical and, as yet, unrecognized role in mediating the meaning of antidiscrimination law through Employment Practice Liability Insurance (EPLI). My analysis draws from, links, and contributes to two literatures that examine organizational behaviour in different ways: new institutional organizational sociology studies of how organizations respond to legal regulation and sociologic insurance scholars’ research on how institutions govern through risk. Through participant observation at EPLI conferences, interviews, and content analysis of insurance loss prevention manuals, my study bridges these two literatures and highlights how the insurance ﬁeld uses a risk-based logic to construct the threat of employment law and inﬂuence the form of compliance from employers. Faced with uncertain legal risk concerning potential discrimination violations, insurance institutions elevate the risk and threat in the legal environment and offer EPLI and a series of risk-management services that build discretion into legal rules and mediate the nature of civil rights compliance. My data suggest that insurance risk-management services may sometimes be compatible with civil rights goals of improving equality, due process, and fair governance in workplace settings, but at other times may simply make discrimination claims against employers more defensible.