Discrimination remains integral to understanding both how inequality is produced and how it can be remedied in employment settings. Yet like many sociological concepts, the notion of discrimination involves an uneasy mapping of theory to practice. Traditional conceptualizations of discrimination as differential treatment are ill-fitted to the structural and relational nature of much discrimination in the contemporary era. The disparate impact doctrine, which recognizes policies or practices that systematically disadvantage protected groups, picks up some of the theoretical slack, but offers little in the way of conceptualizing individuals’ complex and entangled experiences with inequality at work. In this article, I provide a conceptual reorganization of theories of discrimination, underscoring recent calls to move beyond the confines of the current disparate treatment and disparate impact binary by recognizing the structurally and culturally embedded nature of bias and discrimination. Drawing on recent sociological research as well as my own analysis of legal records and interviews with plaintiffs involved in high-profile sex and race lawsuits settled in the past decade, I illustrate how differential treatment emerges in the context of and enabled by systems of vulnerability and privilege, workplace culture, and compositional asymmetries. I conclude with a discussion of the implications of this framework for antidiscrimination enforcement efforts.