A 24-year-old female with no contributory medical history had been treated by orthodontic alignment and transplantation of the lower left first premolar to the upper left first premolar site to correct for congenitally missing upper premolars. Subsequently, the transplanted premolar was treated by conventional endodontics and apical surgery for persistent periapical periodontitis over a span of 12 years. A combination of conventional endodontic retreatment and periapical surgery resulted in periapical healing. This case outlines the need for careful preoperative case assessment.