Nontraumatic pain in the first metatarsophalangeal joint is frequent and can be debilitating. The metatarsophalangeal joint complex comprises four articulating surfaces including the first metatarsal, the proximal phalanx, and tibial and fibular sesamoids, which are all contained within a synovial capsule. The most common causes of pain are hallux valgus and hallux rigidus. However, other diagnoses, such as functional hallux limitus, sesamoiditis, gout, and inflammatory autoimmune arthritis, need to be considered as well. A systematic approach is key to accurately diagnose the source of pain, which can sometimes be the result of more than one condition. The most important clinical information to obtain is a focused history, meticulous clinical examination based on understanding the precise anatomy and biomechanics of the first metatarsophalangeal joint, and analysis of the relevant imaging. Each pathology has a different treatment algorithm, as such, understanding the pathoanatomy and biomechanics is important in forming an effective treatment plan.