Using interview and focus group data (N = 44) from three study sites, we locate prostitution diversion program (PDP) professionals within logics of punishment and governance. While critical research on problem-solving justice emphasizes professionals' performative and quasi-therapeutic roles, inadequate attention has been paid to the contradictory logics of their roles. Involvement in a diversion program reinforces underlying assumptions about whom they are working with and what those people need, in ways that we argue require critical distance. Professionals exploit the paradox of assistance through coercion, and exhibit what we identify as “targeted sympathy.” Targeted sympathy enhances the ability of these professionals to use their discretion to help their clients, but it also elevates a narrow set of acceptable problems and interventions. Created with an understanding of street-based sex workers as victims, PDPs also rely on hyper-responsibilization, expecting defendants to bootstrap themselves over systemic hurdles with virtually no resources. Thus, while targeted sympathy may indicate a movement away from the “othering” that pervades contemporary penality, it continues to decontextualize individuals and assign blame and accountability.