Enthesitis is a cardinal feature of spondyloarthropathies. The Achilles insertion on the calcaneus is a commonly evaluated enthesis located at the hindfoot, generally resulting in hindfoot pain and possible tendon enlargement. For decades, diagnosis of enthesitis was based upon patient history of hindfoot or posterior ankle pain and clinical examination revealing tenderness and/or enlargement at the site of the tendon insertion. However, not all hindfoot or posterior ankle symptoms are related to enthesitis. Advanced imaging, including magnetic resonance imaging (MRI) and ultrasound (US), has allowed for more precise evaluation of hindfoot and posterior ankle conditions. Use of US in diagnosis has helped confirm some of these cases but also identified other conditions that may have otherwise been misclassified without use of advanced imaging diagnostics. Conditions that may result in hindfoot and posterior ankle symptoms related to the Achilles tendon include enthesitis (which can include retrocalcaneal bursitis and insertional tendonopathy), midportion tendonopathy, paratenonopathy, superficial calcaneal bursitis, calcaneal ossification (Haglund deformity), and calcific tendonopathy. With regard to classification of these conditions, much of the existing literature uses confusing nomenclature to describe conditions in this region of the body. Some terminology may imply inflammation when in fact there may be none. A more uniform approach to classifying these conditions based off anatomic location, symptoms, clinical findings, and histopathology is needed. There has been much debate regarding appropriate use of tendonitis when there is no true inflammation, calling instead for use of the terms tendinosis or tendonopathy. To date, there has not been clear examination of a similar overuse of the term enthesitis in conditions where there is no underlying inflammation, thus raising the need for more comprehensive taxonomy.