Historically, in high-risk patients with cardiovascular disease, anticoagulants have been used in order to reduce the risk of stroke or other ischemic complications. However, despite this seemingly simple solution, drug selection and dosage control may provide a unique challenge when it comes to the anticoagulation therapy of individual patients. In this case report, a patient with multiple underlying conditions and two previous stroke episodes was admitted due to decompensated heart failure and was treated with anticoagulants to reduce the risk of developing secondary stroke(s). The initially prescribed anticoagulative agent, acenocoumarol, was discontinued and subsequently replaced with enoxaparin due to unstable INR and undiagnosed anaemia. Unfortunately, newer anticoagulants were contraindicated in this patient due to previous implantation of the mechanical aortic valve. This study reveals and discusses the conundrum faced in prescribing anticoagulants to patients with multiple conditions of underlying diseases. Despite the aforementioned hurdles, anticoagulant therapy in these patients is crucial in avoiding potential life-threatening complications including myocardial infarction and secondary stroke; proper prescription decisions may ultimately decrease morbidity and improve the quality of life of these high-risk patients.