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This paper aims to identify how rural digitalization influences social innovation in the context of the Global South. Using qualitative research methods, we examine two cases of digitalization in rural areas in Indonesia, which represent differing types of digital technologies and economic activities. Our findings show that the use of digital technologies in livelihood strategies stimulates new social and institutional practices in rural areas. As digital technologies that are adopted differ in both cases, the complexity of adoption and the digital literacy and skills required also vary. Such a complexity generates challenges and hardships for the community, but at the same time, it provides room for expedited learning and urges them to fight the challenges collectively. This nurtures reflexivity between agents and stimulates the legitimation of new practices regarding the adoption of digital technologies and their ability to solve social problems. Cultural values clearly play an essential role in this process. Openness and courage to change facilitate agents to build legitimacy, whereas strong cultural values tend to maintain existing practices in a community. [ABSTRACT FROM AUTHOR]