Insertional Achilles tendinopathy (IAT), often called enthesopathy, is difficult to treat and can cause severe problems for the athlete. IAT is a separate diagnosis from midportion Achilles tendinopathy. IAT can coexist with bursitis from any of three bursae around the heel: retrocalcaneal, subcalcaneal, and retrotendinous as well as with inflammatory alteration within the fibroadipose tissue of Kager’s fat pad and an exostosis on the calcaneal tuberosity, known as Haglund’s deformity. Underlying inflammatory predisposition and altered hindfoot biomechanics account for the majority of cases with IAT. The Achilles insertion itself consists of four distinct tissue zones: dense fibrous connective tissue, transitional uncalcified fibrocartilage, calcified fibrocartilage, and finally bone. Pathophysiological alterations include increased release of inflammatory substances and ingrowth of nerves and blood vessels into the fibrocartilage, which in healthy condition is without neuro-vascular structures. Diagnosis of any underlying disorder as well as adverse drug effects is essential before analysis of coexisting inflammatory structures, whereby imaging may be helpful to understand the extent of alterations. Evidence-based first line of treatments includes non-surgical management with shockwave therapy and a modified eccentric exercise program for at least 12 weeks. Calcitrant cases can be handled with mini-invasive and open surgeries to address all pathologies involved.