The comorbidity of obsessive compulsive disorder (OCD) and schizophrenia is an intriguing clinical phenomenon. Such presentation arguably deserves to be recognized as a distinct subgroup of schizophrenia with a possibly different set of challenges and treatment needs. This report describes a patient who had OCD before schizophrenic changes were observed. His continued struggle with his illness despite bouts of minor successes illustrates the complexities of this clinical entity. in managing this patient, we faced several clinical dilemmas including diagnostic ambiguity, issues with pharmacotherapy and difficulties in rehabilitating a patient from a family with high expressed emotion.