Orthograde root canal retreatment is the first-line conservative option when endodontic failure or risk of reinfection is present after prior treatment. We report the management of a maxillary right central incisor (tooth 11) in a 59-year-old male, asymptomatic, with a misfitting metal-ceramic crown placed ~30 years earlier, a cast metal post, and an inadequate root filling. Under rubber-dam isolation, recurrent caries were removed and complete gutta-percha removal was performed. Working length was established at 17 mm, followed by biomechanical instrumentation and activated irrigation with 5.25% sodium hypochlorite and 17% EDTA, alternated with saline. Calcium hydroxide was used as an intracanal medicament at the first visit; at the subsequent appointment, three-dimensional obturation was achieved using cold lateral and vertical compaction with gutta-percha and a bioceramic sealer (MTA Fillapex). A provisional seal was placed and definitive restoration was planned immediately to prevent coronal leakage. Immediate postoperative evolution was uneventful, without pain or swelling. As no evident periapical lesion was observed, the prognosis was considered favorable and consistent with reported success rates when effective disinfection and adequate corono-apical sealing are achieved. This case underscores the importance of identifying etiologies correctable via an orthograde approach, implementing standardized irrigation protocols, ensuring early coronal coverage, and coordinating prosthetic rehabilitation in a multidisciplinary manner to preserve structure and function. Clinical and radiographic follow-ups at 6 and 12 months, and annually thereafter, are recommended to document retreatment success. Coordination with periodontics and prosthodontics optimizes definitive rehabilitation.