At least three fracture types occur in the proximal fifth metatarsal: the Jones' fracture, the proximal diaphysial stress fracture, and the tuberosity avulsion fracture. Each has distinct characteristics. The diaphysial stress fracture is commonly confused with the Jones' fracture, thereby obscuring vital differences in prognosis and treatment. Anatomical and biomechanical characteristics, as well as vascular studies of the proximal portion of the fifth metatarsal, are discussed in an attempt to better understand their diverse healing potentials. Guidelines for treatment are controversial, and must frequently be individualized. Although surgical intervention for certain proximal fifth metatarsal fracture types may speed recovery time, most fractures heal with immobilization. Treatment of displaced, intra-articular fractures, delayed unions, and nonunions usually requires operative methods.