Acquired hemophilia, as opposed to congenital hemophilia, develops in individuals with no previous history of bleeding disorder with almost similar numbers of males and females affected. It is predominantly a disease of the elderly. It is an autoimmune disorder and occurs when the immune system produces antibodies that mistakenly attack healthy tissue, specifically the clotting factors, in particular clotting factor VIII. As a result, affected individuals develop abnormal uncontrolled bleeding into the muscles, soft tissues, and the skin and it can occur spontaneously during surgery, or following trauma, and potentially cause life-threatening bleeding complications in severe cases. The affected individuals may remain undiagnosed or be misdiagnosed, making it difficult to determine the actual frequency of the disorder in the general population. The clinical presentation should suspect it with confirmation by an abnormal coagulation test. Typical laboratory results with a recent onset of abnormal bleeding and an isolated prolongation of the activated partial thromboplastin time (APTT), especially in the elderly and peri- and post-partum women, should raise eyebrows. We present two cases following different symptomatology and emphasize the clinical challenges for junior medical doctors who receive patients on the front end. We hope to emphasize understanding simple coagulation blood results followed by a meaningful discussion with the hematology team towards appropriate and timely management of the bleeding diathesis. We hope this case series report will help junior medical doctors manage patients appropriately and consult with their hematology colleagues.