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The central mechanisms of oversight that exist for prosecutorial misconduct are the courts and, to a lesser extent, state disciplinary boards. Judges are largely responsible, then, for regulating the misconduct of prosecutors that comes to their attention and remedying prosecutorial actions that undermine the fairness of criminal trials. This study explores appellate court opinions and the briefs that support them on judges’ determinations of the harm(lessness) of prosecutorial misconduct. Using data from a random sample of New York appellate court cases decided in 2021 in which prosecutorial misconduct was conceded to have occurred, we conduct an in-depth content analysis to gauge the fidelity of the higher courts to the three specific elements of the harmless error doctrine that ostensibly guides their decision-making. These elements are (a) the severity of the misconduct, (b) the weight of inculpatory evidence supporting the conviction, and (c) the extent to which the misconduct was remedied at trial. The findings of this study contribute to scholarship on legal realism, which posits that legal doctrine is less constraining on judicial outcomes than is typically believed.