Antisynthetase syndrome (ASS) is a rare immune-mediated disorder characterized by interstitial lung disease (ILD) and polymyositis (PM)/dermatomyositis (DM) in association with antiaminoacyl-transfer-RNA antibodies most commonly anti-JO-1 antibodies. We present a case of a 67-year-old man who had uncontrolled type 2 diabetes and complained of coughing, dyspnea, and fever. The primary health center (PHC) physician diagnosed him with bilateral pneumonia based on a chest X-ray. After receiving multiple antibiotics over the course of a month, the patient was referred to us with nonresolving pneumonia. The patient later developed proximal muscle weakness and features of “mechanic's hand” and strongly positive for anti-JO-1 and anti-RO52 antibodies with high creatinine phosphokinase (CPK) levels and features of organizing pneumonia (OP) with bilateral pleural effusions which led to diagnosis of ASS. The patient was started on oral prednisolone and then switched to mycophenolate mofetil, which resulted in a significant difference in both clinical and radiological results. Furthermore, ASS presenting as OP with bilateral pleural effusion is a rare finding, especially as the first manifestation. This report highlights the significance of having an autoimmune workup, comprehensive medical evaluation, and long-term follow-up on patients to screen them for pneumonia and other ILDs.