We examine whether individual differences in needs for security and certainty predict conservative (vs. liberal) position on both cultural and economic political issues and whether these effects are conditional on nation-level characteristics and individual-level political engagement. Analyses with cross-national data from 51 nations reveal that valuing conformity, security, and tradition over self-direction and stimulation (a) predicts ideological self-placement on the political right, but only among people high in political engagement and within relatively developed nations, ideologically constrained nations, and non-Eastern European nations, (b) reliably predicts right-wing cultural attitudes and does so more strongly within developed and ideologically constrained nations, and (c) on average predicts left-wing economic attitudes but does so more weakly among people high in political engagement, within ideologically constrained nations, and within non-Eastern European nations. These findings challenge the prevailing view that needs for security and certainty organically yield a broad right-wing ideology and that exposure to political discourse better equips people to select the broad ideology that is most need satisfying. Rather, these findings suggest that needs for security and certainty generally yield culturally conservative but economically left-wing preferences and that exposure to political discourse generally weakens the latter relation. We consider implications for the interactive influence of personality characteristics and social context on political attitudes and discuss the importance of assessing multiple attitude domains, assessing political engagement, and considering national characteristics when studying the psychological origins of political attitudes.