This article explores episodes in Tasmania's communications history, the reasons it has been chosen to lead the deployment of the National Broadband Network and the crucial role of the Basslink cable, which began providing wholesale communications services to and from the island in July 2009. It then examines the most recent round of measures to improve communications in the State in the decade from 1996. These measures, funded from some of the proceeds of the privatisation of Telstra, favoured Tasmania because of the make-up of the Senate at the time. Despite this attention, continuing dissatisfaction with the state of telecommunications in Tasmania highlights the scale of the challenge for those now attempting again to conquer the remoteness that has been Tasmania's fate since European settlement.