Anticoagulants are commonly associated with hemorrhagic complications. However, rare hypersensitivity drug reactions associated with direct oral anticoagulants (DOACs) in form of cutaneous reactions such as urticaria as well as angioedema can have significant burden owing to increase in morbidity and mortality. Angioedema can be allergic, hereditary or idiopathic and can occur in isolation, in combination with urticaria as contributing component of anaphylaxis. With increase in the use of DOACs over warfarin as choice of anticoagulant in the treatment of atrial fibrillation (AF) as well as venous thromboembolism (VTE), recent post marketing surveillance has identified several reports of adverse drug reactions. This case report describes the clinical course of patient being treated for VTE, who experienced rivaroxaban-induced urticaria and angioedema. We further provide evidence for cross-reactivity to dabigatran manifested as significant cutaneous reaction. Patient was transitioned to warfarin with enoxaparin bridge and tolerated it well without any complications.