Advanced internal resorption affecting the crown of teeth may result in the appearance of a 'pink tooth', which, when located in the root canal, can perforate the external root surface. Therapeutically, this condition represents a clinical challenge and normally requires a combined endodontic and surgical focus. Presented herein are cases of double 'pink tooth' which appeared at different times after orthodontic treatment. In the most severe case, upon radiographic examination and computed tomography, the maxillary right central incisor presented an internal resorption, extending from the pulp chamber to the root middle third. After pulp removal, the debridement of the defect was performed using a 2.5% sodium hypochlorite solution, a #80 Kerr file, and an ultrasonic tip ST-17, aided by a surgical microscope. During the cleaning process, various sites of periodontal communication were identified. Upon controlling the hemorrhaging, the root canal was completely filled with White mineral trioxide aggregate. Within the 3-month follow-up treatment, a pink spot appeared on the maxillary left central incisor, which received conventional root canal therapy. Clinically and radiographically, over 18 months of follow up, both cases responded favorably to the proposed treatments. Therefore, it is important to monitor the patient due to the fact that pulp and periodontal sequelae can develop at varied moments after orthodontic treatment. Furthermore, with the current technology and biomaterials, it is possible to resolve cases with extensive internal perforating resorption through endodontic treatment.