The chapter contributes to the literature and discussions on the regional engagement of universities, providing empirical evidence on academic engagement and how these academics can be motivated and encouraged by regional policy. The chapter specifically asks the question how do entrepreneurial universities create (or do not) frameworks which enable purposive actions by academic actors acting as institutional entrepreneurs to participate in regional development outcomes. The chapter draws upon case studies of three universities all recently actively promoting regional entrepreneurship activities in various ways at the institutional level. This chapter identifies the key tensions and dynamics of the entrepreneurial university’s behaviour to propose a first reflection on how regional policy can be both supportive and steering for institutional entrepreneurs. The chapter concludes that because the connections between institutional entrepreneurs and regional partners are vital to collaboration undertaken – regional policy should devote more resources to building these critical links.