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This paper studies how police officers document stopped motorists’ races to illustrate both the complexity of racial classification and policing’s self-interest in legitimacy. Matching 735,166 traffic stops from Florida with drivers’ voter records via probabilistic linkage, I compare officer- documented with drivers’ self‐identified races across groups. Mismatches occur most prominently among drivers self-identifying as Asian and Hispanic for these groups’ permeable and blurry boundaries. In contrast, White and Black motorists are documented mostly the same as how they self-perceive. However, the ambiguity of racial classification alone cannot explain all discrepancies. Despite typically consistent classification, a spike in recording self-identified Black motorists as White appeared in early 2012 and lasted until 2014. Tracing this puzzle through abductive reasoning, I leverage the February 2012 high-profile killing of Trayvon Martin in Florida for its unique relevance. Results from an interrupted time series analysis (n = 22,606 stops) confirm a large post-scandal increase in misclassification, significant only for self-identified Black people and in the direction favorable for law enforcement. I argue that in police race data, strategic anomalies can be hidden within a broader set of seemingly inevitable ones. This insight portrays the challenges of both the task (i.e., racial classification being differentially non-intuitive) and the project of state legibility (i.e., legitimacy being part of the institutional incentive), wherein the latter can co-opt the former and shape administrative data production.