In 2019, The Open University (henceforth, The OU), based in Milton Keynes in the UK, celebrated its 50th anniversary. Since 1971 it has pioneered the delivery of Higher Education in prisons and other secure settings. Some 50 years on, in 2021 there is much to celebrate and still more to learn. In this article we briefly review the establishment of the OU in 1969 and explore how it has maintained access to higher education in the prison system. It draws from a collection of essays and reflections on prison learning experiences developed by OU academics and former and continuing OU students in prison (Earle & Mehigan, 2019). We begin by outlining the unique features of the OU and the circumstances of its establishment in the post-war period in the UK. We then present an account of its work with students in prison in the UK (and elsewhere) and conclude with some critical reflections on the place and prospects of higher education in an expanding Higher Education sector and an escalating preference for carceral punishment in the UK. No country on Earth can match the penal preferences of the United States, but the UK's habit of slipstreaming behind its massive carceral bulk tends to obscure the fact that the UK punishes more people with imprisonment, and with longer sentences, than any other Western European state. It also manages to exceed the United States in rates of racial disproportionality in its carceral population (Phillips, 2013). Despite these outlier features in incarceration, a silver lining to the carceral cloud can be found in The OU's pioneering work with imprisoned men and women.