The following case is a presentation of a patient with several diagnostic challenges related to an evolving medical history. In childhood, our patient received a diagnosis of narcolepsy with hypnic hallucinations after a prolonged period of uncertain diagnoses. While progressing through adolescence, our patient developed worsening hallucinations which led to further diagnostic challenges, which ultimately resulted in a diagnosis of concomitant schizoaffective disorder. At each step, our patient demonstrated clinical signs and symptoms which were difficult to untangle from other medical history. This case is meant to help highlight sleep disorders and the challenges they present in the neuropsychiatry space. We underline the difference in and overlap of hallucinations occurring in narcolepsy and in psychotic disorders. We also discuss more common sleep medicine diagnoses and treatments that are likely to arise in a neuropsychiatric context. Lastly, we discuss considerations for the neuropsychiatry practitioner that might arise when managing patients with sleep disorders.