Around the world, various correctional jurisdictions are struggling to enable the delivery of higher education into prisons. At a time when universities are moving increasingly online, very often access to the internet is restricted or disallowed in correctional environments. Four universities, all leading distance education providers in the countries in which they are based, are delivering higher education into prisons using technology to varying extents. This paper reports on regional differences in the provision of distance education into prisons, particularly using technology, in Australia, the United Kingdom, Turkey and Nigeria. In these four jurisdictions, there are significant differences in prisoner access to computer hardware, personal devices and to the internet. How these differences impact on the delivery of distance education is explored with an examination of various learning initiatives and lessons learned.