Abstract To break away from techno-institutional lock-in in climate change and in other sustainability problems, many have focused on innovation in technological ‘niches’. The destabilisation of the incumbent ‘regime’ has been neglected and external ‘landscape’ pressures under-analysed. With this in mind, this article examines the factors of regime destabilisation and forms of regime resistance in past technological transitions in energy and transport. It analyses 23 energy (electricity, heat & chemicals) and 11 transport (drive chain, networks, fuels & land planning) transitions pre-1990. Furthermore, in order to properly frame these results and make any “lessons from the past” applicable to the present, this article includes an assessment of current sustainability trends. The key lessons from past energy transitions are that regime outsiders with the right ideology and influence on the market can destabilise the energy sector, which has traditionally had strong incumbents. As incumbents are weakened, past transport transitions show that further change may come from emphasising the Health and Lifestyle benefits of sustainability transitions.