While thromboembolism and bleeding appear, at first glance, to be hematological processes at opposite ends of the clinical spectrum, they share many commonalities of relevance to palliative care teams. Both are increased in the malignant state, particularly with metastatic disease, and consequently confer a significant symptom burden, resulting in high level of distress for patients and carers. Furthermore, they are often the cause, or contributory cause, of death and frequently complicate care at the end of life. The evidence base for the management of cancer-associated thrombosis (CAT) has increased significantly over the past 15 years, yet few studies have included or considered patients with advanced cancer or those nearing the end of life. With respect to the management of bleeding at the end of life, particularly terminal hemorrhage, management is informed by little more than case reports and expert opinion. This chapter comprises of two sections. First, it provides an overview of the management of bleeding in the palliative setting with particular focus on terminal hemorrhage. The second section focuses on the treatment and prevention of venous thromboembolism in the advanced cancer setting, including the management of patients with recurrent thrombosis, thrombocytopenia, and bleeding. It will also review the new oral anticoagulants and consider their place in CAT management.