This chapter examines how the concept of moral luck can inform decisions about granting second chances after ethical missteps. Drawing on the work of Nagel and Williams, the chapter explores how factors beyond an individual’s control can influence both the occurrence of unethical behavior and our moral judgments of it. Four types of moral luck—constitutive, situational, resultant, and relational—are outlined and applied to real-world cases in organizational contexts. Constitutive luck concerns character traits shaped by genetics and upbringing; situational luck pertains to the ethical challenges individuals face or avoid; resultant luck addresses outcomes that influence moral judgments; and relational luck highlights the social context and presence of ethical dissenters. The chapter integrates attribution theory to analyze how people explain misconduct, contrasting internal (personal) and external (situational) causes. Examples include cases from academia, consulting, and finance, demonstrating how appeals to moral luck can be used to explain—but not necessarily excuse—unethical actions. Ultimately, the chapter underscores the need for decision-makers to carefully weigh explanations of behavior, the presence or absence of responsibility, and the ethical dynamics of the organizational environment when considering whether to offer someone a second chance.