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Hereditary hemorrhagic telangiectasia (HHT) is a rare autosomal dominant vascular disorder characterized by mucocutaneous telangiectasias and arteriovenous malformations (AVMs) affecting multiple organ systems. Clinical manifestations commonly include recurrent epistaxis and chronic iron deficiency anemia, while complications such as gastrointestinal (GI) bleeding, high-output cardiac failure, stroke, and venous thromboembolism may occur. Management can be further complicated when an anticoagulant is indicated. We present a case of an 84-year-old female Jehovah's Witness with known HHT, heart failure, and atrial fibrillation who was admitted with worsening exertional dyspnea. Baseline investigations revealed type 1 respiratory failure and elevated D-dimer, and imaging confirmed the diagnosis of massive pulmonary embolism with right heart strain. In light of this diagnosis, she was started on split-dose low molecular weight heparin (LMWH); however, management was significantly constrained by her history of recurrent epistaxis and new-onset GI bleeding, as well as refusal of blood transfusion in accordance with her religious beliefs. Despite standard interventions by ENT to control her nasal bleeding, including cauterization and topical medications, she developed melena and continued to regress afterwards. Anticoagulation was hence discontinued at that time to minimize any further risk of bleeding, but her condition continued to deteriorate. Blood transfusion was discussed but was declined, consistent with the patient's advance directive. Supportive and palliative measures were initiated, but the patient subsequently passed away following clinical decline. This case highlights the complex clinical and ethical challenges of balancing thrombosis and hemorrhage in patients with HHT, particularly when standard interventions are not an option. It highlights the importance of individualized risk-benefit assessment, multidisciplinary involvement, and early engagement with hospital liaison services in Jehovah's Witness patients to make sure that treatment aligns with patients' personal beliefs, and this can prevent any delays in considering life-saving treatment, making sure that patients are well informed of the possibility of any adverse outcome beforehand. Additionally, it reflects the need for continued research into safe and effective alternatives to transfusion of blood products in patients where current standard treatment options, although effective, do not have the same clinical impact.