Cognitive insight refers to awareness of one's own thinking. Research has found deficits in cognitive insight in schizophrenia but studies of its links with positive symptoms and delusions have been equivocal. One possibility is that the association of cognitive insight with positive symptoms and delusions is moderated by other factors. To explore this issue this study examined whether level of socially naive self-appraisal moderated the relationship of two forms of cognitive insight, self-reflectivity and self-certainty with delusions and positive symptoms. Participants were 92 adults, with diagnoses of schizophrenia or schizoaffective disorder, who were administered the Positive and Negative Syndrome Scale, self-deceptive subscale from the Marlowe-Crowne Social Desirability Scale and the Beck Cognitive Insight Scale. Stepwise multiple regressions with the interaction term of the predictive and moderator variables suggested that social naiveté moderates the relationship between self-reflectivity and self-certainty with positive symptoms in general. Moreover, association between self-certainty and delusions was also moderated by social naiveté self-appraisal. All models were significant after controlling for willful impression management as well as a measure of executive function. Results suggest that higher levels of self-certainty are a risk factor for having greater positive symptoms including more severe levels of delusions, when one has a view of oneself that is not tempered by the perceptions of others. Concerning lower levels of self-reflectivity it may be that this combined with a socially naïve view of oneself leaves persons less inhibited when they are tempted to accept unusual thoughts and perceptions as accurate. Implications for treatment are discussed.