This article argues that understanding current approaches to sex offender risk management and its operationalization must account for front line situational decision-making practices and the culture from which they develop and operate. The research utilizes a mixed-methods approach, combining an online questionnaire survey ( N = 227) with a series of semi-structured interviews ( N = 27) with members of the police service of England and Wales. Analysis identifies ambivalence about the effectiveness of the current system of categorizing sex offenders and suggests concerns about accountability and a lack of resources results in discretion being used to engage with but also negotiate policy in practice. The article suggests that the task for sex offender risk management is to create classification tools that work with this discretion rather than against it.