Posterior ankle pain is a common foot and ankle problem faced by orthopaedic surgeons. It can have many causes, including posterior ankle joint pathologies (synovitis or osteochondral lesion), ankle impingement (posterior, posterolateral, or posteromedial), flexor hallucis longus pathologies, peroneal tendon problems, posterior tibial tendinopathy, Achilles tendon pathology, posterior subtalar tarsal coalition, or tarsal tunnel syndrome. Most of these pathologies can be managed effectively by an endoscopic approach. The classic endoscopic approach is the 2-portal posterior ankle endoscopy with the portals at the medial and lateral side of the Achilles tendon. This is performed with the patient in prone position. In this technical note, we describe the details of endoscopic approach to the posterior ankle via lateral portals. This allow flexibility of patient positioning (supine, prone, or lateral). It is particularly effective for the management of posteromedial ankle impingement without the risk of injury to the posterior tibial neurovascular bundle. Moreover, any concomitant peroneal tendon pathology can be managed via the same lateral portals.