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A mounting body of literature suggests that legal cynicism regarding police effectiveness and legitimacy has pervaded disadvantaged urban communities. The approximately 600,000 formerly incarcerated individuals released annually who navigate the challenging reentry terrain are disproportionately concentrated in distressed neighborhoods. Distrust of the law and those who enforce it can help shape residents’ perceptions as negative sentiment travels swiftly via informal social networks. In-depth conversations with returning citizens indicate that situational context largely shapes returning citizens’ willingness to report hypothetical and actual crime to the police. Preliminary study findings suggest that the likelihood of crime reporting increases when the victim is a woman, child or helpless individual. We contribute to scholarly discourse by exploring how strategic avoidance of police impacts how returning citizens choose to distance themselves from non-criminal justice institutions as a collateral consequence. Understanding returning citizens’ avoidance strategies is critical for informing effective public safety approaches and successful reintegration programing.