The papers and commentaries constituting this special issue offer new insights into speculative urbanism from the perspective of two southern metropolises. Based on an international and interdisciplinary collaboration comparing speculative urbanism in central and peri-urban Jakarta (Indonesia) and Bengaluru (India), and interrogating the literature triggered by a seminal 2011 paper by Michal Goldman, this issue extends existing speculative urbanism scholarship in four ways. First, the papers in this special issue take a multi-scalar approach, placing speculative urban practices within the broader spatio-temporal conjunctural contexts shaping their emergence. Second, extending currently economistic framings, they show how speculation also is socio-cultural. The diverse actors engaged in speculative urbanism do not simply seek to accumulate wealth; they do so with aspirations in mind for differentially imagined, but yet-to-be-realized, urban/peri-urban futures. Third, they highlight how speculative urbanism involves a broader range of actors than the usual suspects (developers and financial institutions), including land brokers, individual landlords, the state and its actors, and residents displaced from informal settlements. Fourth, they draw attention to diverse objects of urban speculation; not only land and property, but also more-than-human phenomena such as urban socio-ecologies and socio-technical networks.