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Over the past four decades, life without parole sentencing has moved from the periphery to the core of American imprisonment. Today, it exemplifies a penal space for ‘violent’ and ‘serious’ offending untouched by current waves of bipartisan sentencing reform and death penalty abolition, a region called upon to capture and dam the social tensions the challenged policies once held in check. With an eye to the present, this paper examines the history of life sentencing and other practices under which prisoners have lacked a reasonable expectation of release, as a means of uncovering the ground on which life without parole came into being. Drawing from historical materials concerning American penal policy and reform, I develop five models of perpetual penal confinement. One aim is to generate interpretive tools to animate and guide empirical research, for better articulating, operationalizing, and analyzing the complex phenomenon we refer to today as ‘LWOP’. The paper also illustrates the overlooked but central role that natural life sentences have held in some of the most influential and systematic penal theories—perpetual confinement was often critical to the architecture of theorized penal systems even as it was presented, and in practice operated, until recently, on the margins.