Complications of gastrostomy tube placement and enteral feeding are common. However, most are minor and without serious adverse effects, such as superficial skin infections, peristomal leakage, tube dislodgement, and minor bleeding. Misplacement of a gastrostomy tube through the anterior and posterior gastric walls is a rare but serious complication. If not detected and corrected, it could have serious and potentially life-threatening consequences for the patient. We present a case of a 78-year-old male with acute stroke and resultant severe oropharyngeal dysphagia requiring long-term enteric feeding tube placement complicated by a malpositioned gastrostomy tube that was placed through both the anterior and posterior walls of the stomach during a laparoscopic procedure, resulting in coffee-ground hematemesis on the first postoperative day. Investigation revealed the malpositioned tube, which was surgically repaired on time without significant morbidity.