This study tested the reproduction hypothesis that the Internet produces positive payoffs for those in privileged social positions, while disfavoring marginalized communities. Using a national sample of adult Internet users (n = 419), the first premise of this study investigated the impacts of (1) sociodemographic status, (2) Internet access indicators, and (3) their interactions on the variations of capabilities, as assessed through discrete measures of Internet-related personal information skill and knowledge. The second premise introduced the factor of individual motivation in interaction with sociodemographics and Internet access indicators. Hierarchical logistic regressions showed manifest age and gender disparities, with the significant interactions indicating that Internet access exacerbates existing offline status disparities. The reinforcement of digital divide was particularly salient in knowledge dimensions. The findings are discussed with regard to the conditions that incubate systematic differences in people’s ability to understand or resist data surveillance. Implications for policy initiatives are offered.