This is the first in a new series of case reports that will present real scenarios from our community hospital. The cases are chosen to highlight clinical dilemmas and offer review and perspective on what is currently known about the topic. We present the case of a 55-year-old Caucasian male who presented to the emergency department of our community hospital for worsening dyspnea. Evaluation in the Emergency department revealed a diagnosis of extensive pulmonary emboli in the pulmonary vasculature. The patient was admitted to the ICU. A clinical decision was made to initiate treatment with low-dose tissue plasminogen activator (tpa) followed by intravenous heparin infusion. Several hours later the patient developed significant epistaxis. A decision was made to stop the heparin infusion. Later that day, the patient had abrupt clinical deterioration with subsequent cardiac arrest and did not recover. We discuss the classification and treatment of acute pulmonary embolism, the management of epistaxis in an anticoagulated patient, and the clinical conundrum of balancing active bleeding in patient requiring anticoagulation.