Vaccine-induced thrombotic thrombocytopenia (VITT) is a rare yet fatal side effect associated with adenoviral vector vaccines for coronavirus disease of 2019. We report a case of VITT in a previously healthy 43-year-old woman occurring 10 days after receiving the Johnson and Johnson (Ad26.COV2.S) vaccine. She presented with right-sided weakness, aphasia, and left gaze deviation. Computed tomography angiography of the head and neck revealed complete occlusion of the left internal carotid artery, left anterior carotid artery, and left middle cerebral artery with hemorrhagic conversion and midline shift. Pertinent laboratory results revealed acute thrombocytopenia and an elevated d-dimer level. She tested positive for platelet factor 4 (PF-4) antibodies, and a Doppler ultrasound revealed a deep vein thrombosis of the right femoral and popliteal veins. With these findings and the timing of vaccine administration, she had met the full criteria for VITT. While the crucial immediate treatment of VITT is therapeutic anticoagulation, its application for this case was contraindicated due to evolving hemorrhage and the need for an urgent decompressive craniectomy. An inferior vena cava filter was inserted, and intravenous immunoglobulin was administered, resulting in a suboptimal rise in platelet counts. She was then successfully treated with the addition of high-dose steroids and rituximab, eventually displaying therapeutic anticoagulation more than 2 weeks after the diagnosis. Two years after this diagnosis, she had slowly recovered from VITT. Her PF-4 antibodies are negative, and she remains only on prophylactic anticoagulation. This case highlights the importance of early recognition of symptoms to establish the correct diagnosis and the complexities of acute treatment of VITT in patients with contraindications to early therapeutic anticoagulation.