The ability to predict the surgical difficulty of lower third molar extraction facilitates the design of treatment plans by minimizing complications and improving the preparation of patients and assistants in terms of the postoperative management of inflammation and pain. The aims of this study were to evaluate the value of panoramic radiographs in predicting lower third molar extraction difficulty and technique and to determine if the experience of the practitioner had any influence on this predictive ability. Fourteen dental practitioners with varying levels of experience evaluate the difficulty of lower third molar extraction in a group of patients using a 100-mm visual analog scale (VAS) and a modified version of a surgical difficulty scale. The results were then compared to postoperative scores calculated using the same scale. A tendency to underestimate the difficulty of procedures that was more pronounced in observers with greater levels of experience was observed. A low level of agreement between preoperative and postoperative evaluations using the surgical difficulty scale as well as an association between difficulty assessed preoperatively using the VAS and difficulty assessed postoperatively using the surgical difficulty scale was also found. The use of panoramic radiographs does not allow practitioners to accurately predict lower third molar extraction difficulty and technique, regardless of their level of experience.