Jejunal diverticulitis is a rare form of diverticulosis that occurs in the jejunum. Ileal diverticula are a type of false diverticula that are mostly asymptomatic and are usually discovered on imaging as incidental findings. Jejunal diverticula are typically difficult to diagnose pre-operatively due to their indolent and asymptomatic nature. The etiology of this condition is unclear, although some are believed to be genetic if diffuse. When symptomatic, patients may present with vague symptoms. This requires a high index of clinical suspicion because imaging results are usually negative. Management often requires surgical intervention in the presence of complications. Our case highlights a rare case of jejunal-ileal diverticulosis with inward involution causing Witzel tube (jejunostomy tube, or J-tube) obstruction and failure, along with partial obstruction of the small bowel.