Complicated small-bowel diverticulosis is a rather uncommon cause of upper abdominal pain. It may lead to symptoms presenting with an acute onset or to chronic and nonspecific complaints. As the presentation is often similar to other pathologies (acute appendicitis, pancreatitis, or acute cholecystis) and in many cases diagnosis is made on basis of surgical findings, careful analysis of the imaging landmarks may be warranted to aid in the early stages of detection. In this report, we present clinical and morphological findings in three patients where small-bowel diverticulitis was surgically proven. The relevant literature is reviewed, and typical imaging properties are discussed.