This paper offers a reflection on 15 years of policy change in the City of Cape Town aimed at fostering sustainability from the perspective of a City practitioner. The persistent continuation of unsustainable outcomes, despite ongoing policy reforms, is understood as a combination of the emergence of wicked problems, within a changing local government mandate, in the absence of a transformation of institutional structures, tools and approaches. While the approach to policy reform in Cape Town has focussed on reducing substantive uncertainty through its knowledge-based approach, we show that in the context of an expanding local government mandate, sustainability becomes an aspect of many departments’ directive resulting in strategic uncertainty. The untransformed traditional line-function-based structure of local government in turn works against integration between departments (fundamental for addressing non-linear wicked problems), thus promoting institutional uncertainty. In addressing this combination of strategic and institutional uncertainty, our findings indicate that integration has to happen in the policy stage in order for sustainability principles to be implemented in relevant departments; that implementation requires resourcing across the institution, and ought to be included in departments’ targets; and that competing and conflicting rationalities underpin the policy–practice gap. It is suggested that a first step in breaking down the strategic and institutional uncertainties would be to foster shared values through creating deliberative spaces within the City in which debate, discussion and learning can occur.