This chapter describes the process, tensions, and impact of the development of regional units of Estonian universities, focusing on one of the smallest among them, Kuressaare College located on an island, placing it in the periphery of the periphery. Despite Saaremaa island having only 30,000 inhabitants, its college and associated competence centre co-operated effectively and in a well-focused way. This co-operation has built on effective synergy of university, businesses, and the local community underpinned by political support.