The quantity and quality of social contacts have been related to self-esteem, and both social relationships and self-esteem have been implicated in the pathways to paranoia. However, how social relationships interplay with self-esteem to trigger paranoia is not well understood. This study aims to investigate whether different measures of social connectedness (social support, loneliness, and desired friendship), as well as the frequency of social contact, impact paranoia and other positive and negative psychotic-like experiences (PLE) through the indirect effect of self-esteem. Data from a sample of 169 nonclinically ascertained participants oversampled for schizotypy scores were analyzed using two different approaches: retrospective trait-like and ecological momentary measures of social connectedness. Results showed that self-esteem mediates the pathways from poor social support and social longing, but not from loneliness, to paranoia and other cognitive PLE. In contrast, pathways from social connectedness to perceptual PLE and negative PLE were not mediated by self-esteem. Results were consistent across trait-like and momentary measures. Finally, self-esteem was not implicated in the pathways from the frequency of social contact and paranoia or other forms of PLE. These results provide a comprehensive picture of how social connectedness drives specific symptoms of psychosis through self-esteem. Findings underscore the need to explore separately the quality and quantity of social relationships and suggest that the subjective experience of meaningful social bonds is key social determinants of mental health. Therefore, addressing inadequacies of social connectedness could substantially improve symptomatic and functional outcomes of psychosis.