Background: Small bowel neoplasms (SBN) are rare but pose a significant diagnostic challenge. The routine upper endoscopy delays the diagnosis, and most cases require multiple investigations increasing the health care burden., Case Summary: A 74-year-old man presented with two months of progressively worsening postprandial bilious emesis and epigastric abdominal pain. He underwent outpatient evaluation with upper endoscopy and a computed tomographic enterography. The first endoscopy did not enable us to recognize the small bowel mass, leading to a diagnostic delay of two months. He subsequently developed a complete intestinal obstruction. A Second look upper endoscopy done with a push enteroscopy showed an apple core-like mass suggestive of a possible malignant neoplasm at the distal duodenum/proximal jejunum., Conclusion: Therefore, more sensitive, and specific diagnostic modalities like push enteroscopy, capsule endoscopy, and deep enteroscopy should be considered in case upper endoscopy is not conclusive., Competing Interests: Conflicts of interest No conflict of interests., (© 2023 Greater Baltimore Medical Center.)