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While considerable scholarly attention has been devoted to the negative effects of pretrial detention in terms of conviction and sentencing outcomes, it is unclear why these patterns exist. To better understand the mechanisms linking pretrial to adverse case outcomes, I explore recent scholarship related to the: 1) causal effects of detention on conviction and sentencing; 2) social ecology of bail; 3) pains of pretrial detention; and 4) pressures to plead guilty. After reviewing the literature, I outline several additional possible mechanisms linking pretrial detention to case outcomes that warrant additional analysis. Building upon recent innovations in the literature, I outline novel areas for research on the pretrial detention and punishment nexus.