Tracheoinnominate fistula (TIF) is a rare condition with significant potential for mortality if surgical intervention is not immediate. We present two cases of successfully managed TIF. Both cases involve ligation and resection of the innominate artery at the TIF followed by a pectoralis major muscle flap. In both cases, success was largely due to a high index of suspicion and immediate control of the bleeding with transport to the operating room for surgical repair. The history, aetiology, and pathogenesis of TIF are reviewed, yielding an algorithm for recommended management of TIF.