This study aims to explore the influencing factors of multidisciplinary digital social innovation (DSI) in the OECD (Organization for Economic Cooperation and Development) member countries in light of the socio-technical system transition theory. It sets up the eight variables of the four areas that comprise the DSI, and then identifies the causal conditions (arrangements) based on the empirical findings through the fuzzy-set multi-conjunctural analysis. In short, it concludes that, if OECD member countries have high level of democracy and e-participation, high GDP and business-friendly environment, high social expenditure, and high level of ICT (Information and Communication Technology) development and patent applications, they are highly likely to achieve a sufficient level of digital social innovation. This study underlines that the result of combined arrangement explains that the DSI can be more properly characterized by the multi-level and structured approach of the socio-technical system transition that goes beyond the fragmentary approach of existing innovation theories and the current related academic field. Moreover, this study reveals that the social factors (including the social capital variable) that have attracted attention from previous studies may have little effect on the DSI. In essence, it suggests that citizen interaction and social change can be newly formed through technological innovation in a multi-dimensional way, and that more in-depth discussion regarding the new context of ‘digital citizen’ might be required.