The environmental state is confronted with the task to facilitate a comprehensive sustainability transformation of society. It is argued that structural barriers akin to an invisible ‘glass ceiling’ are blocking any such transformation. First, the structure of state imperatives does not allow for the addition of an independent sustainability imperative without contradiction. Second, a distinction is introduced between ‘lifeworld’ and ‘system’ sustainability, showing that the environmental state’s contribution to state legitimation is to provide an environmentally sustainable lifeworld, which is, however, predicated on a fundamentally unsustainable reproductive system. Finally, a deep explanation of the glass ceiling is offered, based on a constructivist model of state legitimation that locates the main barrier in the ‘paradox of representation’ at the core of the modern state. From this, conclusions regarding possible futures of the environmental state and societal transformation are drawn.