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Research finds that cisgender women typically receive fewer and more lenient sanctions than cisgender men. This finding extends to formal sentencing guidelines: women are more likely than men to receive downward departures, which can entail shorter sentence lengths, blended sentences, or other alternative sanctions. Less clear are the reasons driving this imbalance in punishment. Gender disparities in the commission of discretionary guideline deviations may reflect the legal system’s role in perpetuating heterotypical gender norms. Various explanations, such as the chivalry hypothesis, the context hypothesis, and the focal concerns perspective, are explored to investigate this possibility. The current study uses United States Federal Sentencing Commission data (1999-2023) to examine whether (1) legal and extralegal characteristics can explain differences in guideline departures, (2) the impact of these characteristics differs by defendant gender, and (3) there are gendered trends in the reasons specified for the deviation. Following existing research, we expect legal factors to significantly impact sentencing decisions more than extralegal characteristics, regardless of defendant gender. In the explanations for departures, however, we predict that female defendants will be more likely than male defendants to be “departed” for extralegal reasons that highlight and reinforce gender stereotypes. Theoretical and policy implications will be discussed.