Patients with cancer have a well-documented increased risk of developing venous thromboembolism (VTE) due to a variety of factors that can include tumor-induced hypercoagulability, which varies by tumor type; venous stasis, or vascular compression by tumor; and therapies used to treat the underlying malignancy. Advances in cancer detection and treatment have improved survival, even if patients are not cured, so that cancer in many patients can be viewed as a chronic disease. This has resulted in patients living longer, but also developing complications. In addition to VTE, these complications can include an increased bleeding risk related to both tumor and treatments. Managing the competing risks of thrombosis and bleeding can be difficult in any patient and even more so in the cancer patient. Although many advances have been made recently in specific management of cancer-associated thrombosis (CAT), each patient can present a unique combination of bleeding and thrombotic risks, and treatment must be tailored to accommodate these individual risks. In the cases below, we review common clinical situations and the data that guide management.