This chapter investigates which factors affect the timing of guilty pleas for defendants under the current regime of a quantified sliding scale of sentence discounts. Certain vulnerable defendants are found to be more likely to plead guilty such as young adult defendants. It is discovered that the stages of the criminal process preceding plea taking have been found to significantly affect plea outcomes. Defendants who have confessed to the police and who are represented by publicly funded lawyers are more likely to plead guilty, and to plead guilty earlier. Furthermore, the extant literature also points to defendants remanded in custody to be susceptible to pleading guilty earlier as well. Under a guilty plea process that features a sliding scale of sentence discounts, different factors may serve as potential pressures for defendants to plead guilty, and to plead guilty as early as possible.