Surgery of the Achilles and posterior tibial tendons requires finesse to achieve optimal function. Although superficial in anatomic location, various critical neurovascular structures exist in close proximity. The superficial blood supply is fragile, requiring a delicate touch to prevent problems with wound healing. Damaged tendon tissue often is friable, making it difficult to sew or anchor. Adjusting the tendon length to the appropriate tension requires good judgment and affects long-term outcome through power and range of motion. Finally, surgery on these two tendons significantly affects function of the ankle and longitudinal arch, where small changes are magnified into large changes in maintaining normal gait. The current authors review the complications encountered in various common surgeries of the Achilles and posterior tibial tendons.