The management of surgical patients with thrombotic or bleeding diathesis is a common and challenging clinical scenario. Physicians are often asked to manage patients undergoing surgery who are receiving oral anticoagulant therapy with vitamin K antagonists or direct-acting oral anticoagulants (which confers an “acquired” bleeding tendency), or, more rarely, patients undergoing surgery who have a history of an adverse drug reaction to anticoagulants such as heparin-induced thrombocytopenia, or an inherited bleeding disorder. In the cases below, we review common clinical situations and discuss perioperative management strategies, with data and recommendations to support these strategies when available.