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Retreatment is common in endodontics. The purpose of this article was to classify the different clinical situations encountered in retreatment cases and relate them to the outcome after an observation period of 24 months. A total of 425 patients (452 teeth) from 451 patients, consecutively admitted for root-canal retreatment, were monitored during a 24-month period. All teeth (254 molars, 107 premolars, and 91 single-root anterior teeth) were divided into two major categories: teeth with modified anatomy from previous endodontic treatment (root-canal-morphology altered) and teeth in which no significant anatomical changes were made by the former endodontic treatment (root-canal-morphology respected). Although the overall success was 69.03%, the success in the root-canal-morphology-respected group was 86.8% and in the root-canal-morphology-altered group 47% (Mann-Whitney U test p < 0.0001). The clinical success of an endodontic retreatment seems to depend on whether alterations in the natural course of the root canals were caused by previous root-canal treatment.