Context: Adrenal hemorrhage is a recognized yet rare complication associated with antiphospholipid syndrome (APS), an autoimmune disorder characterized by the presence of antiphospholipid antibodies that increase the risk of thrombosis. The incidence of adrenal hemorrhage in patients with APS has a diagnostic yield of approximately one-third, indicating that it may often go unrecognized in clinical practice. Traditionally, the management of APS has relied on anti-vitamin K therapy, such as warfarin. However, the advent of direct oral anticoagulants (DOACs) has prompted discussions about their use as an alternative. Recent clinical guidelines, however, strongly advise against the use of DOACs in patients with APS due to concerns over their safety and efficacy in preventing thromboembolic events. Case Presentation: This case study describes a 53-year-old woman with a history of venous thromboembolism who was treated with apixaban, a direct oral anticoagulant. She presented with acute abdominal pain and symptoms suggestive of adrenal insufficiency. Initial evaluations revealed significant changes in her clinical condition, leading to further diagnostic imaging. A CT scan demonstrated bilateral adrenal hemorrhage, which was a surprising finding given her anticoagulation therapy. Subsequent laboratory tests indicated a positive triple antibody profile, confirming a diagnosis of primary antiphospholipid syndrome. This case is particularly noteworthy as there have been limited documented instances of adrenal hemorrhage in patients receiving chronic anticoagulation with apixaban. The presentation of bilateral adrenal hemorrhage in the context of APS adds a crucial dimension to the understanding of the disease and its management. Conclusion: This case highlights the potential for serious complications, such as adrenal hemorrhage, in patients with antiphospholipid syndrome, particularly those treated with direct oral anticoagulants. It underscores the necessity for clinicians to remain vigilant for such rare yet significant events in the management of APS. Additionally, this case raises important questions regarding the appropriateness of DOACs in this patient population, especially given the latest recommendations against their use. Increased awareness and further investigation into the implications of anticoagulation strategies in APS patients are warranted to improve patient outcomes and safety.