Objective Identify previously unreported factors that predict the need for post–acute care after free flap reconstruction of the oral cavity. Study Design Retrospective cohort study. Setting Single academic medical center. Methods A total of 134 patients with head and neck disease involving the oral cavity underwent free tissue transfer for reconstruction between August 2012 and October 2015. All patients had a tracheostomy placed at the time of surgery. Data were collected, including demographics, perioperative risk factors, and social variables. Univariate and multivariate logistic regression were used to identify risk factors for needing post–acute care. Results Of 134 patients, 37 (28%) required post–acute care upon discharge, and 97 of 134 (72%) were discharged home with assistance. Multivariate logistic regression revealed that lack of family support (adjusted odds ratio [AOR], 32.12; 95% CI, 13.75-274.90; P = .002), tracheostomy tube at discharge (AOR, 13.70; 95% CI, 3.20-58.44; P < .001), government insurance (AOR, 3.85; 95% CI, 1.13-13.11; P = .031), hospital stay >10 days (AOR, 3.52; 95% CI, 1.25-9.90; P = .017), and increasing age (AOR, 1.11; 95% CI, 1.04-1.18; P = .003) were significantly associated with post–acute care need. Conclusion: Lack of family support, tracheostomy tube at discharge, government insurance, hospital stay >10 days, and increasing age are independently associated with the need for post–acute care following free flap reconstruction of the oral cavity. Physicians, social workers, and nurse case managers are positioned to identify patients at high risk for needing post–acute care and to reduce the duration of hospitalizations.