Pediatric Helicobacter pylori infection represents a small proportion of disease that is otherwise decreasing in the developed world. Typical presentations have been well-described in the literature. We report a 15-year-old male who presented with jaundice, anemia, dark urine, and poorly characterized abdominal pain and was found to have obstructive jaundice secondary to a duodenal ulcer resulting from H. pylori infection. Obstructive jaundice is a seldom reported complication of duodenal ulcer, particularly in children. This report reviews H. pylori infection, outlines complications of peptic ulcer disease, and illustrates the rarity of obstructive jaundice as a presenting sign of duodenal ulcer in children.