Case Report: Krukenberg tumor is a metastatic adenocarcinoma of the ovary that classically arises from the gastrointestinal tract, most often as a metastasis from the stomach as the primary origin, followed by colon. Krukenberg tumors are very rare malignant tumors of the ovary, only accounting for 1-2% of all ovarian malignancies. They tend to present with bilateral involvement. The most common presenting symptoms are abdominal pain, distention, and ascites, secondary to the large ovarian masses. Postmenopausal vaginal bleeding is a rare presenting symptom of a Krukenberg tumor. The diagnosis is commonly delayed until late in the disease progression. We present a case of a 77-year-old woman with stage IV metastatic adenocarcinoma of lower GI with mesenteric involvement and pulmonary nodules. Her disease was confirmed by mesenteric mass biopsy and was histologically CK20 positive, CDX positive, and CK7 negative. She underwent eighteen rounds of palliative chemotherapy with oral capecitabine (Xeloda) over the course of fifteen months. Sixteen months after the initial diagnosis, imaging uncovered a new cystic pelvic mass measuring 15x13x12 cm, decreased mesenteric mass, increasing liver lesion, metastasis to the left adrenal gland, and minimal ascites. She has had vaginal bleeding. Patient underwent total abdominal hysterectomy with bilateral salpingo-oophorectomy and small bowel resection by gynecological oncologist. The left ovary was involved by metastatic adenocarcinoma, 15 cm, consistent with small bowel origin. The small bowel resection showed adenocarcinoma, 3.3 cm in size with serosal invasion arising in an adenoma. Patient is planned for chemotherapy with irinotecan in palliation. Our case demonstrates a rare case of small bowel adenocarcinoma later presenting as a Krukenburg tumor.