Recently updated guidelines for Atrial Fibrillation (AF) outline that percutaneous left atrial appendage (LAA) occlusion with the Watchman device may be a reasonable alternative for those who have contraindications to long-term oral anticoagulation. However, optimal periprocedural antithrombotic therapy remains disputable, particularly in patients who are ineligible for oral anticoagulation or those with history of intracranial hemorrhage (ICH). We present the case of a 67-year-old male with a history of ischemic stroke with hemorrhagic conversion and permanent AF, who was treated with the Watchman device and subsequently developed device related thrombus and recurrent ischemic stroke. We discuss the dilemma and review the literature regarding anticoagulation for device related thrombus in this patient with increased bleeding risk, given his history of ICH. His course and antithrombotic strategy are described and despite the use of anticoagulation with warfarin in the setting of recurrent ischemic stroke, he did not develop hemorrhagic transformation. He also did, ultimately, achieve device related thrombus resolution on repeat Transesophageal Echocardiogram (TEE). This case supported the use of warfarin for device related thrombus in the setting of ischemic stroke and history of ICH. However, evidence-based guidelines for periprocedural antithrombotic regimens in patients with high bleeding risk have yet to be released and further research is needed.