Digitalisation is likely to change established economic development processes. This raises questions about the distribution of the potential welfare gains from industrialisation highlighted by, among others, the UN Sustainable Development Goal (SDG) 9 ‘sustainable industrialisation’. In parallel, industrialisation and digitalisation must be made environmentally sustainable if other pressing sustainability goals, such as climate change mitigation (SDG 13), are to be met. Yet, under the current political and economic system, efficiency gains in material resources and energy associated with digitalisation are prone to aggregate to macro-level growth (‘digital rebound’) that may exacerbate ecological harm of industrialisation, rather than alleviating it. In this article, applying the CPERI/CSPK approach (cultural political economy of research and innovation/complex systems of power-knowledge approach), we argue that digital rebound should be a central research parameter in research on digitalisation and sustainability. Thinking strategically about different models of digitalization, which we call the ‘human-machine associational model’ and the ‘machinic micro-efficiency model’, may enable not only change in the trajectory of digitalisation itself. Yet, it could simultaneously but indirectly address the dominant regime of political economy at system-level, which will either propel or contain digital rebound. We conclude the article by opening up lines of enquiry, for both research and practice to approach a ‘system-questioning’ model of digitalisation.