The surgical patient with multiple medical comorbidities challenges the clinician with difficult treatment decisions. Diseases prevalent in contemporary society, such as diabetes mellitus and hypertension, introduce numerous management considerations during the perioperative period. Postoperative infection, extended hospital stay, and anesthetic complications are only some of the unfavorable outcomes that are well documented in the medically compromised surgical patient. Surgical outcomes after the treatment of odontogenic infection in the patient with comorbidities may be significantly compromised. In patients with poorly controlled diabetes, disruptions in collagen metabolism, the formation of granulation tissue, endothelialzation, and capillary basement membrane thickening may develop. The known microvascular complications are multisystemic, affecting, but not limited to, the cardiovascular, renal, and immune systems. The present report describes the case of a patient with poorly controlled diabetes who developed significant postsurgical complications after failed endodontic therapy and the extraction of a left mandibular first premolar.