We present the case of a 43-year-old male with a history of poorly controlled type II diabetes who presented with altered mental status, urinary incontinence, and diabetic ketoacidosis (DKA). Initial brain imaging studies were negative for acute intracranial pathology; however, the next day, the patient was found to have left-sided paralysis. Repeat imaging studies revealed a right middle cerebral artery infarct with hemorrhagic conversion. Given that the rate of reported strokes in the setting of DKA in adults is limited, this case report affirms to discuss the importance of prompt recognition, evaluation, and adequate treatment of DKA to prevent neurological complications, as well as the pathophysiology behind the etiology of DKA-induced stroke. This case also underscores the importance of early recognition and missed strokes in the emergency department (ED) and emphasizes the need for stroke evaluation in patients with altered mental status even though an alternative diagnosis is apparent to avoid anchor bias.