Background: Insertional Achilles tendinosis is a clinical entity that commonly occurs with other posterior heel disorders such as retrocalcaneal borsitis, Haglund deformity, intratendinous ossification and pretendinous borsitis. Complete detachment and reconstruction of the Achilles tendon was evaluated as a method of treatment for this condition. Methods: Seventy-five patients (81 heels) were treated over a 5-year period for chronic insertional Achilles tendinosis. These were divided in two groups: a nondetached group (26 patients, 31 heels, average age 55 years) included all patients with debridement of the Achilles tendon with no or partial detachment of the tendon, and a detached group (49 patients, 50 heels, average age 56.1 years) that included all patients with complete detachment, debridement, and reattachment with suture anchors of the Achilles tendon associated with proximal V-Y lengthening of the proximal aponeurosis. Sixty-one patients (65 heels) were contacted for an interview questionnaire, 22 patients from the nondetached group (26 heels) and 39 patients from the detached group (39 heels). The average followup for the nondetached group was 47 months and for the detached group 33 months. Items evaluated included pain, activity limitation, gait change, walking distance, return to sport or work, and level of satisfaction. Results: No statistically significant differences were noted in relation to any of the items evaluated. In the nondetached group, the satisfaction rate was 92%, and 8% were dissatisfied. In the detached group, 74% were completely satisfied and 18% were satisfied with reservations. Eight percent were dissatisfied. Complications included minor wound dehiscence (one in the nondetached, five in the detached group), wound infection (one in the nondetached group, two in the detached group) and sural neuritis (two in the detached group). Conclusions: Complete detachment of the Achilles tendon and reattachment with suture anchors and a proximal V-Y lengthening was a reliable and effective method of treatment for severe chronic insertional Achilles tendinosis as was debridement of the tendon insertion without detachment for less severe involvement. Copyright © 2006 by the American Orthopaedic Foot & Ankle Society, Inc.