In recent decades, advocates for police reform on the political left and right have proposed numerous changes to how street-level policing operates. One such proposed reform, which has been adopted in jurisdictions nationwide, is “proactive policing,” that is, policing strategies based on the notion that by proactively regulating minor offenses, the police can reduce both serious crime and fear of crime in the community. Yet, as with many proposed police reforms, researchers have not undertaken a through benefit-cost analysis of proactive policing. This article lays out strategies for estimating the impacts of proactive policing, including direct, indirect, and distributional impacts. First, I describe quasi-experimental approaches, which entail partnerships between researchers and police departments and would be particularly useful when a municipality is considering a move to proactive policing in the first instance, expansion of small-scale proactive policing to a larger area, or the introduction of particular new tactics. Second, I describe nonexperimental retrospective approaches, including conventional regression analysis, which can also allow researchers to estimate the effects of proactive policing. I discuss potential threats to validity for both strategies. I close by describing the data that researchers wishing to engage in benefit-cost analysis of proactive policing would need in order to do so.