To analyze how education and employment risk influence social policy preferences, we proceed in two steps. We first show empirically that insider/outsider divides and education are crosscutting: atypical forms of employment are also common among certain highly educated seg- ments of the labor force. However, one may question whether atypical employment among the highly skilled is indeed related to labor market disadvantages (which the notion of ‘outsiderness’ implies), or whether it is just an unproblematic, flexible form of employment. Hence, we subse- quently demonstrate that labor market vulnerability is associated with labor market disadvantages in terms of income, job satisfaction, replaceability, and training opportunities also among the highly educated. In a second step, we examine the preferences of the cross-pressured group of highly educated outsiders with regard to three distributive principles of social policy: redistribu- tion, activation and social insurance. In contrast to existing studies, we do not analyze preferences for ‘more’ or ‘less’ welfare state, but preferences for distinct distributive principles of the welfare state.