The Authors describe two cases of alleged malpractice due to overfilling. The aim of this article is to underline some medico-legal aspects regarding the quantity of extruded material which may be considered acceptable and the consequent damage to the patient. Two cases are presented here: In the first case, the dentist’s liability is clear due to excessive extrusion of endodontic material beyond the apical region combined with incomplete obturation of the canals. In the second case however, because two different dentists were involved, establishing the connection of causality between their work and the damage reported by the patient was not easy. This situation makes it difficult to establish the limits of potential responsibility, coupled with the complete absence of radiographic signs of periapical rarefaction and the small quantities of material beyond the apex. From a medico-legal point of view, a dentist may be held responsible for compensation and financial expenses of a patient for restoration of damage resulting from a dental procedure. Italian guidelines offer no indications as to when overfilling should be considered the result of a procedural error, or if it fits within the range labelled as “acceptable” and this gap offers extremely subjective interpretations of legal consultants. So, it would therefore be useful to adopt more precise qualitative/dimensional parameters, keeping in mind that the guidelines offer therapeutic recommendations and are not rigid protocols.