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Although research establishes that penal state interventions lead to an array of detrimental institutional consequences, theoretical accounts have yet to articulate the role of micro-level agency. To explain this process, I advance the concept of “collateral decision-making,” whereby individuals adopt decisions with adverse institutional consequences due to criminal justice embeddedness. Individuals must reframe how they navigate aspects of an institution to mitigate negative criminal justice institutional experiences. To illustrate this process, this article utilizes a unique, in-depth interview sample of 65 pretrial detainees who are simultaneously embedded in a distinct pair of state institutions—jails and criminal courts. The findings unravel the empirical puzzle of why pretrial detainees have substantially worse plea agreement outcomes than their free counterparts, revealing that pretrial detainees reframe how they navigate case resolution in criminal courts—adopting unfavorable plea agreements to mitigate negative pretrial detention experiences such as participation in a gauntlet of physical violence, exposure to the criminal-legal misery of peers in court holding tanks, poor quality of life in jail, and primary caretaker obligation failure. The findings illustrate the propensity of the penal state to shape agentic behavior in other institutional contexts and the salience of multiple institutional embeddedness for understanding social disparities.