Ashley Smith’s experience in the adult prison system flowed from certain of its systemic features. This article considers whether and how it is possible to reconcile the basic commitments of sentencing law, including the legal aims of punishment, with that systemic portrait. The youth court that ordered Smith’s transfer to adult custody relied upon an idealized conception of adult imprisonment, just as ordinary adult sentencing courts do. Judges purport to stipulate the severity of punishment, but tend not to consider how prison conditions will shape the severity of the sanction. Even where a particular defendant is likely to face unique difficulties in custody, courts tend to take notice in limited and rare ways. Smith’s experience in adult custody challenges us to more clearly identify, and to consider extending, doctrinal sentencing rules that represent a judicial concern with the effects and prospects of imprisonment in particular cases.

A “just punishment” is increasingly structured by actuarial probability frameworks. Actuarial risk technologies are often characterized as having supplanted much of practitioners' discretionary decision making with structured, quantitatively derived decision-making templates. Some scholars maintain that the transition to risk-based penality has led to “deskilling,” “scientification,” and “erosion of professional discretion,” or even to the elimination of criminal justice practitioners' use of professional discretion. This paper uses data from 71 semi-structured, open-ended interviews with criminal justice professionals to analyse how the introduction of risk tools shapes but does not eliminate discretion. We argue that risk tools are not simply imposed on criminal justice practitioners; instead, practitioners actively resist and embrace risk technologies and temper the impact risk tools have on their discretionary decision making. We maintain that the adoption of risk technologies reflects a negotiated process whereby practitioners welcome the professional advantages that these technologies afford while affirming the centrality of experience and clinical knowledge in decision making. We show how practitioners differentiate between the standardization intended by risk assessments and their own experiences and clinical knowledges, and how they exercise their discretion in an effort to mitigate the perceived discriminatory effects of the risk assessment. Thus, although risk tools are appealing to practitioners because their supposed “objectivity” makes them more defensible to the public, the adoption and use of these tools in the context of professional decision making is more complex and contradictory than much of the theoretical literature has assumed.