This chapter aims to challenge histories of automation that depict it as a teleological movement from industrial automation to ‘smart’ machines; moving from manual to ‘cognitive’ automation. Instead, we demonstrate that technological innovation is never straight-forward, but characterised by failures and dead ends as well as specific choices that are anchored in the social and political context rather than a natural evolution towards the ‘best’ technological solutions. Drawing on popular visual depictions of automation since the 1950s, we focus on critical junctures of automation - such moments where it becomes apparent that automation develops into a different direction than initially imagined. Focusing on these two critical junctures, while following the evolving dominant discourse of computerization and automation since the 1950s, we show that an important part of technological change is constituted by meaning-making processes that shape and make the implementation of new technologies possible.