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The overwhelming majority of convictions result from guilty pleas with roughly 97% of all convictions arising from guilty pleas (Peterson & Redlich, 2022). As systematic data is lacking on plea offers and what leads to offers being accepted or declined by the criminal justice experienced, questions remain as to why those with experience persist in foregoing their right to trial. To address this gap, we successfully administered surveys containing hypothetical plea scenarios to more than 250 inmates in several jails across New York State. Our study was focused on establishing a proof of concept for surveys of this kind with incarcerated populations while also testing three key manipulations: (1) assigned innocence/guilt, (2) plea sentence for 90 days in jail or 3 years of probation, and (3) the deal framed as a gain, neutrally, or as a loss. Of the three tested manipulations, the clearest variation was present for assigned guilt or innocence with nearly two times as many respondents assigned to the guilty condition taking a plea deal as compared with those assigned to the innocent condition, although innocent plea rates were still higher than 40%. Implications for plea research and defendant decision making of the criminally experienced are discussed.