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Abstract
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.

In prisoner litigation, straightforward victory is rare. Win or lose, prisoners most often remain in the custody of officials who continue to wield substantial power over them. And even where claims succeed, courts may design legal tests in ways that are deferential over time to the claims and preferences of prison authorities. Prisoners prevailed in two recent Supreme Court of Canada cases that involved, first, post-sentencing legislative changes to parole entitlements and, second, a decision to transfer a prisoner to a higher security setting. In Canada (Attorney General) v. Whaling, the Court protected prisoner expectations at sentencing regarding the length of time to be spent in custody, and declared the retroactive application of a more restrictive parole scheme to be constitutionally invalid. Simultaneously, however, the Court endorsed a view that prison officials and legislators are largely free to alter the conditions of confinement over the course of sentence administration. While the fitness of a sentence is significantly impacted by prison conditions, Whaling suggests that this is not a topic for sentencing judges to address or constitutional principles like non-retroactivity to protect. In Mission Institution v. Khela, the Court emphasizes the importance of prisoner access to habeas corpus as a vehicle to challenge the liberty-depriving decisions of prison officials. Simultaneously, however, the Court holds that reasonableness is the standard of review for at least some parts of the decision challenged in habeas corpus. The implications of importing a deferential administrative law standard into the constitutional vehicle of habeas corpus remain unclear at this stage. At the very least, the decision marks a shift away from the historical distinctiveness of the writ of habeas corpus, and implies that the decisions of prison employees should attract deference even in cases in which constitutional rights are engaged.