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Anomalies of the thoracic venous system are rare and usually discovered incidentally, but they become clinically relevant in the case of patients requiring cardiac device implantation. Persistent left superior vena cava is considered the most common venous drainage abnormality, with several anatomical variants that generate technical difficulties during pacemaker or defibrillator lead placement. We report a case of an isolated persistent left superior vena cava with abnormal drainage into the left atrium, associated with a hypoplastic right-sided superior vena cava, in a patient scheduled for permanent pacemaker implantation. Considering the patient’s anatomical characteristics, a transvenous approach proved unfeasible and the procedure was successfully accomplished via the surgical placement of a left ventricle epicardial lead. We aim to emphasize the clinical importance of such venous anomalies and to discuss the practical implications and challenges derived from these types of conditions, especially in the field of electrophysiology.