While pleading guilty has become ubiquitous in criminal trial courts, limited research has focused on the plea process and the factors that influence guilty plea convictions. Numerous theoretical accounts of the plea process highlight the importance of the court actors and their interactions. Based on this research, the current study analyzes the impact of courtroom actor familiarity and similarity on the chosen mode of disposition and the time to disposition. The findings demonstrate that similarity among the actors and familiarity between the prosecutor and judge increase the odds of a plea disposition and reduce the days to disposition. However, familiarity of the defense attorney seems to impede on the informal plea process, such that cases are more likely to proceed to trial when the defense attorney is more familiar with the other actors.