Rural digitalisation is often approached from a structural research perspective, focusing on broadband infrastructure and socio-economic contextual conditions. Such perspectives tend to neglect the agency of individual and collective actors in these areas. Our comparative case study addresses this gap by focusing on Digital Pioneers in two structurally different rural regions in Germany. Our analysis of 40 semi-structured qualitative interviews with selected pioneers is based on the research question of how these key actors access resources to realise digital social innovation. A categorization of our data shows three general patterns: Access to motivational resources on an individual level, access to network-based resources through various types of social relationships, as well as access to region-based resources by analytically linking agency and socio-spatial contextual conditions. We conclude that Digital Pioneers can become intermediary key players in regional governance constellations. At the same time, additional policy support or reversion is needed to facilitate access to network- and region-based resources in particular.