This chapter explores the history of the South Atlantic island of St Helena, with a particular focus on developments in its informational connectivity, dating from the era of the East India Company and encompassing undersea telegraph cables, radio and (since 2023) high-speed broadband internet access, amongst others. Despite its geographical isolation, the island has by no means always been isolated from, or even peripheral to, global networks of transportation and information flows. However, St Helena’s history provides evidence for a persistent and profound separation between technology and local culture. Several significant investments in ‘connectivity’ have been made in the past, but all have come and gone with little impact being felt by the island’s community and culture. Information networks have exploited the island’s position and remoteness, but mostly for the benefit of colonising powers with very little, if any, diffusion of benefits (‘trickle down’) to the local community.