Many higher education institutions (HEIs) in peripheral regions are surrounded by rural areas where small independent businesses form the core of local industry. Rural entrepreneurs often have little experience from contacts with HEIs, and vice versa, although the potential benefits of such linkages could be considerable. In this chapter we reflect on how HEIs’ engagement with rural entrepreneurs can be developed and organised and what impact such engagement might have on regional green transitions, based on our own experiences from entrepreneurship training at a peripheral university in south-eastern Sweden. The chapter contributes with insights on how small-scale rural entrepreneurship can be supported, ultimately leading to more resilient and flourishing rural areas.