Metatarsalgia is among the most common sources of forefoot pain. Proximal metatarsal osteotomies are an important technique in the armamentarium of the surgeon treating metatarsalgia that has failed nonoperative management. Proximal osteotomies can provide powerful deformity correction with precise control to both shorten and elevate the metatarsal head. However, they can be technically challenging, difficult to attain satisfactory fixation, require increased postoperative immobilization, and can result in transfer lesions. There are numerous described techniques with little supporting evidence and more research is needed to establish the optimal procedure to reliably alleviate patient's symptoms while minimizing complications.