Though almost all convictions are the result of guilty pleas, little research has examined influences on defendant plea decisions. First, we explore how attorney satisfaction and court legitimacy affect defendant choices. Using an experimental approach, we then assess the impact of a defense attorney’s evaluation of a plea offer on the defendant’s willingness to accept a plea, and whether this is moderated by defendants’ individual views. Findings demonstrate that higher attorney satisfaction and higher court legitimacy are associated with higher willingness to accept a plea. Defendant decision-making is also impacted by their attorney’s evaluation of the plea and this influence is moderated by the defendant’s satisfaction with their representation. In line with previous research, we also find differences across guilt indicating that guilty and innocent defendants may have different decision-making processes. Results suggest that guilty plea research should continue to evolve with increased attention to the defendant and their counsel.