Metatarsalgia is a blanket term to describe pain in the forefoot that may have many different etiologies and contributory factors. A careful history, examination, and appropriate imaging are required to make an accurate diagnosis and treat the patient appropriately. Metatarsalgia is a common condition and is more common in women. Many nonsurgical treatments can be implemented as a first line but if these fail then surgery may be undertaken. There are several different lesser metatarsal osteotomies described with little published evidence to recommend one over another, leaving the decision as to which one to use largely to surgeon choice. The surgeon, however, must decide, by using a combination of clinical examination and imaging, whether the desired effect of the osteotomy is to shorten or elevate the metatarsal head or both. Whichever method is employed it is important to maintain or restore the metatarsal cascade to keep even pressure under the lesser metatarsal heads and prevent transfer lesions. Proximal osteotomies are more powerful than distal ones but often that can mean that they are more technically demanding. Many early descriptions of osteotomy techniques did not include any fixation but the results in terms of union and relief of symptoms as well as the prevention of transfer pain appear to be better with fixation. More research is required comparing the different osteotomy techniques to ascertain which can most reliably resolve patients’ symptoms with the lowest complication rate.