Thromboses of the deep veins (DVT) and potential complications are disorders with which physicians need to be well familiarized so they can be recognized and managed. Hypercoagulable states play a significant role in the development of DVT and these disorders must be suspect when thrombosis occurs, especially in the upper extremities. Antiphospholipid antibody syndrome (APS) is one such hypercoagulable state in which autoantibodies are formed against anionic phospholipid complexes. In vivo, these antibodies cause a hypercoagulable state through a number of proposed mechanisms, whereas in vitro they interfere with the assembly of phospholipid complexes, thereby inhibiting coagulation and prolonging various clotting times. Though appearing to be anticoagulated on ancillary testing, patients with APS are actually in a pro-thrombotic state requiring treatment with the anticoagulants heparin and warfarin. This case discussion focuses on the recognition and treatment of thrombotic events in the setting of APS.