The Making the Connection project is aiming to introduce digital technologies into Australian prisons to allow access to digital higher education for incarcerated students. But correctional leadership and custodial personnel, because of the legitimate need to maintain public safety, are highly risk averse, especially when dealing with digital technologies. This paper describes how the project team worked with three levels of correctional leadership across a number of correctional jurisdictions to successfully deploy the project at 20 sites. It elucidates the engagement strategy employed by the Making the Connection project, a crucial factor in the success of the project. It describes the challenges and opportunities encountered with a view to proposing a framework through which university researchers can productively work with correctional leadership to mutual benefit.