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Sentencing departures - instances where court-imposed sentences deviate from established guidelines — have significant implications for justice system consistency and fairness. This paper examines how prosecutors and defense attorneys in Minnesota approach decisions to depart from sentencing guidelines, specifically focusing on four distinct offense categories: Assault 2, Aggravated Robbery, Failure to Register, and Felony Motor Vehicle Operation. Drawing from qualitative interviews with Minnesota criminal justice professionals, this study identifies key factors and contextual considerations that shape departure decisions. Findings reveal both commonalities and offense-specific differences in decision-making processes, emphasizing the complexity involved when balancing individual circumstances against guideline constraints. By illuminating how professional roles and specific offense characteristics interact to influence sentencing outcomes, the study provides practical insights for policymakers and practitioners aiming to enhance sentencing guideline clarity and reduce sentencing disparities.