Anatomic and operative textbooks and current literature do not clearly describe the Achilles tendon interface to the calcaneal tuberosity. We dissected 51 specimens to identify the detailed anatomy of the Achilles tendon insertion. Achilles tendon fascicles expanded from the anterior aspect of the distal Achilles tendon over the retrocalcaneal bursa to the anterior part of the Haglund's tuberosity in nearly half of the specimens. The insertion of the transverse section of the Achilles tendon regularly had a crescent-shape corresponding to the posterior calcaneal prominence. In transverse sections, all specimens had a curved appearance with a radius of curvature ranging from 13.8 mm to 43.6 mm (mean, 20.4 mm) and Achilles tendon extensions to the lateral and medial calcaneal surfaces reached 1.0 mm (mean) and 3.5 mm (mean) anterior in relation to the most posterior point of the calcaneal tuberosity. Knowledge of the arcuate configuration and of the medial and lateral extensions of the plantaris and the Achilles tendon insertion with respect to the transverse plane is important to avoid iatrogenic complications during resection of Haglund's tuberosity.