Tracheostomy is a routinely performed procedure, especially for patients who need long-term intubation, frequent pulmonary suctioning, or airway protection due to neurologic conditions. Despite being commonly performed, tracheostomy can lead to distinct complications that require careful surgical technique and an understanding of individual patient factors. In this review, we focus on the intraoperative complications that have been reported in the literature. We address the incidence, factors linked to a higher preponderance, and the key differences in complications between the open surgical and percutaneous dilatational tracheostomy technique. We also elucidate strategies for anticipating, preventing, and optimizing the treatment of complications.