This chapter discuss how transition management, as a set of epistemic techniques, seeks to persuade urban governance actors to reimagine and reshape socio-technical systems. We first discuss how transition management concepts have been informed by complexity theory, particularly regarding notions of fundamental sustainable change and transformative agency. Conceptually, four epistemic techniques are presented, through which transition management practices challenge and reframe urban systems. An empirical case in Rotterdam (the Netherlands) then illustrates how complexity-based transition management concepts redefine, reimagine and – to some extent – reshape Rotterdam’s mobility, including mobility policy. More specifically, we discuss how transition management concepts politicise mobility (policy) by calling into question car and growth-based planning, while linking physical mobility to issues of economic opportunity and income inequality. Finally, we conclude with some reflections on the complexity applying transition management in urban environments.