Calcaneoplasty is the term used to describe the reshaping of the posterior tuberosity of the heel bone in selected cases of posterior heel pain. Surgical debridement of the retrocalcaneal space and decompression by calcaneoplasty of the posterosuperior tuberosity is an established option for the treatment of retrocalcaneal bursitis caused by chronic pathological impingement between the distal portion of the Achilles tendon and the profile of the posterosuperior calcaneal tuberosity. The first reports of endoscopic calcaneoplasty appeared in the early 2000s. Most of the literature on this topic consists of retrospective case series and few comparative analyses, highlighting high rates of patient satisfaction and very low complication rates. Although prospective comparative studies comparing open and endoscopic procedures are still lacking, the available data also suggest faster recovery and lower complication rates after endoscopic calcaneoplasty compared with open surgery in patients with retrocalcaneal bursitis. Endoscopic calcaneoplasty requires established experience in hindfoot endoscopic techniques to avoid iatrogenic damage to hindfoot anatomical structures and to efficiently progress in the learning curve. Retrocalcaneal bursitis may be associated with varying degrees of pathology of the insertion region of the Achilles tendon, which must be properly diagnosed and treated to avoid postoperative recurrence associated with incomplete treatment.