Acute, or repetitive, compression of the posterior structures of the ankle may lead to posterior ankle impingement (PAI) syndrome, posteromedial ankle impingement (PoMI) syndrome, or Haglund's syndrome. The etiology of each of these conditions is quite different. Variations in posterior ankle osseous and soft tissue anatomy contribute to the etiology of PAI and Haglund's syndromes. The presence of an os trigonum or Stieda process is classically associated with PAI syndrome, whereas a prominent posterosuperior tubercle of the os calcis or Haglund's deformity is the osseous predisposing factor in Haglund's syndrome. PoMI has no defined predisposing anatomical variants but typically follows an inversion-supination injury of the ankle joint. This article discusses the biomechanics, clinical features, imaging, and management of each of these conditions. Magnetic resonance imaging (MRI) provides the optimal tool in posterior ankle assessment, and this review focuses on the MRI findings of each of the conditions just listed.