Informal settlements are particularly vulnerable to environmental hazards, due to the lack of infrastructure such as drainage systems and because residents' homes are built with inferior materials. A number of case studies analyse flood-prone informal settlements, mostly with a focus on describing the flooding, household vulnerabilities and coping mechanisms. Although this is important, it is also acknowledged that better collaborative efforts, both within communities and between communities and local government, are needed to move from coping towards adaptation. In order to better understand the capacities of communities to engage in collaborative efforts, we need to look at issues of governance, political dynamics and leadership. Drawing on insights from 3 years of field visits to three flood-prone informal settlements in Cape Town, this paper first illustrates that, although residents apply coping mechanisms on a household scale, the common spaces of the settlements continue to become flooded. Thereafter, context-specific conditions for engaging in collaborations that could improve adaptation at the community scale are discussed. Community leaders are central actors in this regard as intermediaries between residents and local government or non-governmental organizations, and three factors condition their chances of working towards community-scale adaptation: the location of the settlement, external connections and internal consolidation. Comparing the settlements, these factors show how both macro-policies and micro-politics restrict adaptation. To enable community leaders to work towards community-scale upgrading, macro-policies that establish uneven possibilities for different settlements need to be addressed, in addition to the lack of transparency that fragments micro-politics and trust within the settlements.