Complications associated with digital and lesser metatarsal surgical procedures have been well documented in the literature. These complications may stem from systemic medical, structural, biologic, biomechanical, or iatrogenic causes. The surgeon must be cognizant of all potential complications, including ways to prevent them from occurring and how to manage them when they do occur. This article discusses preventative measures through the preoperative evaluation of the patient, and examines the subsets of complications that may occur after lesser ray surgery that pose a particular management challenge, as well as special complications specific to particular operative techniques.