Hypertensive disorders of pregnancy typically occur in the third trimester, with earlier presentations associated with underlying disorders such as antiphospholipid syndrome (APLS). We describe a case of a young primigravida presenting at 15 weeks 6 days gestation with epigastric pain, vomiting, new-onset severe-range hypertension, and subsequent development of anemia, thrombocytopenia, and transaminitis. Antiphospholipid antibodies (aPL) were triple-positive and imaging was negative for thrombosis. She was treated with aspirin, therapeutic anticoagulation, and ultimately dilatation and evacuation with initial postoperative improvement. Her symptoms returned postoperative day 3 and resolved following re-initiation of therapeutic anticoagulation. The differential diagnosis for hypertensive disorders of pregnancy is wide, particularly in second-trimester gestation, and includes catastrophic antiphospholipid syndrome (CAPS), lupus flare, microangiopathic anemias, and acute fatty liver of pregnancy. This case was an atypical presentation not clearly explained by any of the above diagnoses and required a multidisciplinary approach. Obstetric patients with high-risk aPL must be meticulously investigated with a broad differential to guide diagnosis and treatment.