This open access edited volume is based on the premise that entanglements between current societal, political, technological, ecological, and cultural transformations cannot be sufficiently understood without transforming the modes, forms, and notions of understanding. Conceptually, “uncertain curiosity” is inspired by Helga Nowotny’s Insatiable Curiosity, as it maps trends in the history of knowledge on creative curiosity and its shifting relation to innovation-promoting institutions and societal notions of  un/certain and un/predictable futures. This volume explores epistemic, infrastructural, and cosmological conditions under which the curiosity drive can flourish. Adopting an encyclopedic structure, the contributions engage with terminologies that echo transformation processes and conditions of change by foregrounding the ephemeral, the processual, and the desynchronous and address issues of insurability, vagueness, and ambiguity. This is achieved through a blend of case study research, critical terminological work, poetic engagement with language, and visual culture and discourse analysis through the lenses of artistic research, philosophy, media and cultural studies.