The association between dissociation and psychopathological symptoms is well established, yet studies with inmates are lacking. If higher rates of dissociation and psychiatric symptoms are reported in inmate samples, it is not clear whether they represent two separate, albeit related, characteristics. We examined the association between dissociation and psychopathological symptoms among 320 Italian subjects (122 inmates and 198 community participants) and a Portuguese inmate sample (n = 67). Then, we tested whether dissociation and psychopathology levels were higher among inmates. Both hypotheses were supported, confirming the relevance of dissociative, paranoid, and psychotic symptoms among inmates, as well as their interrelations. Notably, the group difference in dissociation remained significant after partialing out the variance associated with other psychopathological symptoms. Conversely, only the difference in paranoid symptoms remained—marginally—significant when controlling for the influence of dissociation. This finding suggests that dissociation may have unique relevance for the psychological functioning of inmates.