Police disciplinary systems are predicated on the notion of deterrence, particularly that officers more severely sanctioned for misconduct will be less likely to repeat those behaviors compared with less severely or unsanctioned officers. Using retrospective, longitudinal data from a large police department in the northeastern United States, we explore whether this fundamental assumption of police disciplinary systems is supported. Specifically, we examine both the likelihood and timing of complaints filed against officers who had obtained at least one complaint in their career that was sustained (i.e., upheld in an investigation), and compare outcomes of sanction severity on future sustained complaints. The results demonstrate that while a few demographic and complaint characteristics significantly affect the likelihood and timing of future misconduct in expected ways, officers who received more severe sanctions were actually more likely to obtain an additional sustained complaint when compared with nonsanctioned officers. Why this is the case is unclear from the data, but the most plausible explanation is that the perceived injustice of the disciplinary system may actually promote officer deviance.