Abstract Anterior cervical discectomy and fusion surgery is a common and well described surgical procedure, with a well documented risk and complication profile. Here we present a case report of a patient with a concurrent tracheal and esophageal perforation in the setting of ACDF surgery. Our patient developed these complications secondary to hardware failure and underlying cervical osteomyelitis. We hope to not only increase awareness about an uncommon, potentially fatal, complication associated with ACDF surgery but also outline our management algorithm. Our particular patient underwent an initial surgery for tracheal perforation repair, involving the use of a locoregional flap which is outlined in detail. The patient subsequently underwent a second surgery for identification and repair of an underlying esophageal perforation, which utilized a pedicled muscle flap for surgical repair. Here we describe our perioperative management and surgical technique in managing complex complications arising in the setting of anterior cervical discectomy and fusion surgery.