Detachment with reattachment of the Achilles tendon is a common surgery for debridement of retrocalcaneal exostosis, bursitis, and other insertional pathologic entities. The technique involves a midline skin incision on the posterior Achilles to the tendon. The distal Achilles attachment is removed in a U-shaped manner, leaving the medial and lateral flares, but exposing the posterior spur. This midline approach provides excellent exposure and allows for rapid and efficient surgical debridement. The tendon is reapproximated and repaired with a suture anchor to facilitate fixation to the posterior calcaneus. Some surgeons have expressed concerned that the rupture risk could be increased in the postoperative period using this technique. The present study was a retrospective medical record review of 98 patients (100 feet) who had undergone a midline approach with Achilles reattachment after insertional Achilles debridement during a 3-year period. The demographic and comorbidity data were collected and analyzed. The outcome measures were postoperative rupture and the need for revision surgery. The mean age was 51.9 years, and the patients included 59 females (60.2%) and 39 males (39.8%). The complications included 4 rupture or avulsion revisions (4.0%) and 2 recurrent pain and tendinitis revisions (2.0%). The most common repeat repair procedure included hardware removal and a flexor hallucis longus transfer or augmentation. Nine patients (9.0%) had wound complications, 7 (77.8%) of which necessitated incision and drainage. The midline approach with Achilles detachment and reattachment is a safe and effective method of surgical treatment of insertional Achilles pathologic entities. The low reoperation rate of 4.0% will allow foot and ankle surgeons to safely rely on this approach.