Marginalised communities in Aoteaora-New Zealand have been struggling to achieve parity with their more affluent neighbours for several decades. Successive government and NGO initiatives have rolled out subsidised broadband Internet connectivity, advocated for computers in homes and run skills development programs, however there are still significant gaps in digital uptake. Agencies have in many cases completed initiatives and programmes and are “moving-on” from issues of material access into skills development and capability building initiatives and yet the digital divide continues to remain a persistent phenomenon. This paper examines this situation through the lens of two high deprivation-index communities and through critical examination of that data, identifies eight success factors that practitioners and future empirical researchers can use to further frame exploration of this challenge.