As societies become more connected and digitalised, evidence shows that differences in infrastructure quality are growing between urban and rural areas. The constant catch-up of infrastructure and existing social exclusion factors create a double jeopardy in rural areas. Furthermore, as digital technologies are increasingly embedded into economic, political, social, and personal lives, the disadvantages that occur from disconnection manifest differently depending on the social context of an individual, organisation or community. There is a need to improve our understanding of specific contexts of digitally excluded groups and develop targeted policies and programmes. Drawing from fieldwork in rural communities in Australia, this article examines the relationship between limited connectivity, the local context and socio-economic outcomes in rural areas. We suggest a customised policy framework that is responsive to the diversity and uniqueness of local contexts in connectivity and digital inclusion.