The debate on automation in education is also a debate on teachers’ work. Throughout history, promises of labor-saving and efficient automation technologies have been repeatedly promoted, while research at the same time has rather argued that automations will always depend on extensive human labor. In this study, we historicize how automation in education has been related to teachers’ work and with what implications. Based on Sweden’s long history of educational technology, we have drawn on digital and archival materials published from 1957 to the present. By contrasting the policy elements on automation and artificial intelligence (AI) across the past several decades, we show how debates and technologies are dynamically established and naturalized over time, which also risk silencing the critical debates on what the politics of automation and AI means for teachers’ work and for public education. We conclude not only that the automation debate aligns with familiar ‘techno-solutionist’ educational technology histories, including forms of resistance on the technological uptake in education and society, but also that the scale and impact of automation are shifting with the technologies for automation and global platform infrastructures integrated into education. Consequently, one of the main questions is how the critical debate on automating teacher work and education is made possible even under such circumstances.