Existing literature points to guilty pleas leading to plea-trial disparity in sentences, with scholars referring to this as a ‘trial penalty’ or a ‘trial/jury tax’, while courts and policymakers use the terms ‘sentence discounts’ or ‘sentence reductions’. This chapter argues that plea trial and plea-timing disparities have negative consequences for the justice system, as well as that the sentence disparity should be conceptualised as a trial and late-plea penalty. Using the datasets from the Crown Court Sentencing Survey (CCSS) and the Hong Kong District Court compiled for this study, this chapter investigates the effects that the timing of guilty pleas may have on sentence outcomes. Interestingly, a late-plea penalty was found for England and Wales, whereas only a trial penalty was found for Hong Kong. The chapter concludes by discussing the implications of these results.