Reported is a case of a 29-year old Gravida 5 Para 4(4004), 23 6/7 weeks pregnant, known diabetic with hepatic hemangioma, who previously underwent ligation of ruptured esophageal varices, was admitted for the first time on February 21, 2015 due to left-sided hemiparesis. Identifying the cause of the pontine bleed and its possible association with coexisting medical problems was an arduous process since there are no existing management guidelines. Emergency Caesarean Section with bilateral tubal ligation under general anesthesia was done at 35 weeks AOG and a live baby girl was delivered with an Apgar score of 9,9. Magnetic Resonance Angiography (MRA) of intracranial vessels postpartum revealed a Cavernoma. This case is of particular importance due to the following reasons: 1.) Cerebral Cavernous Malformation (CCM) is a rare disease, 2.) There is scant data associating CCM with pregnancy, 3.) Current literature has not reported CCM with Hepatic Hemangioma in a single patient, 4.) No data has linked it with diabetes mellitus, 5.) There are still no management guidelines of CCM in pregnancy, 6.) A multidisciplinary approach is necessary for optimal maternal and fetal outcomes.