This paper draws from two case study informal settlements and their recent Constitutional Court litigation to explore the connection between informal living spaces, democracy, and housing. The temporal element of this development dynamic is examined through the erosion and building of hope resulting from the political actions of the state and the political agency of the poor. This engagement of time as an element of space is considered through residents’ expectations manifested in social processes reflecting either the criticality of hope as a catalyst for bottom-up developmental agency or waiting as a fortification of the top-down status quo.