The paper analyses and compares two transformative moments of technologically-mediated change in East Africa, the construction of the Uganda railway between Mombasa and Lake Victoria (1896-1903) and the introduction of fibre-optic cables that landed into the ports of Dar Es Salaam and Mombasa in 2009. It uses discourse analysis to examine how technologically-mediated connectivity has been represented by political and economic actors during these transformative moments.