Peroneal tendon pathology is commonly seen in patients with underlying pes cavus. The Dwyer calcaneal osteotomy is a useful adjunctive procedure to address the heel varus component of the cavus foot deformity, especially in the presence of concomitant peroneal tendon pathology. The lateralizing heel osteotomy using a wedge resection can effectively reduce future stress on the repaired peroneal tendons, although technical challenges arise when attempting to perform both tendon repair and heel osteotomy through the same incision. Specific principles must be followed to achieve adequate exposure of the desired structures, obtain desired correction of the deformity, and avoid complications such as sural neuritis. In the present report, the surgical principles and technical pearls are highlighted in a pictorial demonstration of preoperative planning for calcaneal wedge resection, incision placement, osteotomy guide pin technique, fixation pearls, and peroneal tendon repair and transfer.