Haglund's syndrome is impingement of the retrocalcaneal bursa and Achilles tendon caused by a prominence of the posterosuperior calcaneus. Radiographic measurements are not sensitive or specific for diagnosing Haglund's deformity. Localization of a bone deformity and tendinopathy in the same sagittal section of a magnetic resonance imaging scan can assist with the diagnosis in equivocal cases. The aim of the present cross-sectional study was to determine the prevalence of Haglund's syndrome in patients presenting with Achilles tendinopathy and note any associated findings to determine the criteria for a diagnosis of Haglund's syndrome. We reviewed 40 magnetic resonance imaging scans with Achilles tendinopathy and 19 magnetic resonance imaging scans with Achilles high-grade tears and/or ruptures. Achilles tendinopathy was often in close proximity to the superior aspect of the calcaneal tuberosity, consistent with impingement (67.5%). Patients with Achilles impingement tendinopathy were more often female (p < .04) and were significantly heavier than patients presenting with noninsertional Achilles tendinopathy (p = .014) or Achilles tendon rupture (p = .010). Impingement tendinopathy occurred medially (8 of 20) and centrally (10 of 20) more often than laterally (2 of 20) and was associated with a posterior prominence or hyperconvexity with a loss of calcaneal recess more often than a superior projection (22 of 27 versus 8 of 27; p < .001). Haglund's deformity should be reserved for defining a posterior prominence or hyperconvexity with loss of calcaneal recess because this corresponds with impingement. Achilles impingement tendinopathy might be more appropriate terminology for Haglund's syndrome, because the bone deformity is often subtle. Of the 27 images with Achilles impingement tendinopathy, 10 (37.0%) extended to a location prone to Achilles tendon rupture. Given these findings, insertional and noninsertional Achilles tendinopathy are not mutually exclusive and impingement might be a subtle, unrecognized cause of Achilles tendinopathy and subsequent rupture.