This chapter introduces an anthology that 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. Inspired by Helga Nowotny’s Insatiable Curiosity: Innovation in a Fragile Future (2008 [2005]), this announcement of Uncertain Curiosity draws links between curiosity and epistemic, political, creative, or strategic un/certainty. As a kind of fugitive glossary, this edited volume begins with an A, suggesting the idea of departure, but it does not end with a Z, fleeing from the hegemonic idea of the encyclopedia born out of the Enlightenment’s assumption of the possibility of achieving certainty through general knowledge. Adopting an encyclopedic structure reflexively, the contributions, which are briefly outlined, engage with terminologies not usually associated with the jargon of global transformation discourse. Instead, they address processes and conditions of change by foregrounding the ephemeral, the processual, and the desynchronous as well as issues of insurability, vagueness, and ambiguity through the lenses of artistic research, philosophy, media and cultural studies.