Intestinal carcinoid tumors are uncommon malignancies which grow slowly and rarely cause any symptoms. Small bowel tumors can, at times, cause bowel obstruction and rarely, bleeding. We present a 52-year-old male who presented to the hospital for evaluation of melena. His endoscopy and colonoscopy came back negative and patient unfortunately failed to get capsule endoscopy as an outpatient. One year later, patient presented with excruciating abdominal pain and was found to have small bowel obstruction with multiple transition points. Patient was found to have four nodular lesions in the small intestine which were found to be carcinoid tumor. Surgical resection definitely improved his outcome and patient did not need adjuvant therapy after surgery. This patient was a diagnostic challenge due to unusual presentation and negative CT scan imaging during both presentations. Carcinoid tumors are highly infiltrating tumors; hence, high degree of suspicion should be kept for earlier detection and better outcome.