Abstract My paper approaches the theme of computational creativity by looking at uncertainty as an epistemic and aesthetic tool that must be examined to address the challenges brought to critical practice by planetary computation. It positions uncertainty as central to how the encounter of the human practitioner with non-human machines is conceptualized, and as a resource for building speculative-pragmatic paths of resistance against algorithmic capture. It proposes ways to cultivate uncertainty and use it as a design material to produce new types of knowledge that question machines’ pre-emptying manoeuvres and resist their capture of potential. The argument proposed is that uncertainty affords the production of new imaginaries of the human-machine encounter that can resist the foreclosure of futures (what will be) and are sustained instead by the uncertainty of potential (what might be) (Munster 2013). Dwelling in a space of potential – Deleuze’s virtual, or what I call a space of ‘maybes’, requires of the practitioner a repositioning of their epistemic perspective and reflecting on the following questions: how can material knowledge be made by engaging with modes of un-knowing and not-knowing in machine interaction? How can these modes of un-knowing and not-knowing be fostered as a critical and political onto-epistemological project of reinventing critical practice for the algorithmic age? (Horl et al. 2021; Hansen 2021, 2015, Pasquinelli and Joler 2020). The paper argues that the machinic unknown should be engaged with - not through the conventional paradigm that pitches human vs machine creativity and attempts to rank and score them through similarities, but rather through a (paradoxical) deepening of the unknowability at the core of the machine (Parisi) and machine’s own incommensurability (Fazi 2020). It then proposes the Chinese notion of wu wei (active non action) (Jullien 2011, 2004, 2000, 1995; Allen 2015, 2011) as a stratagem to experiment with to craft speculative-pragmatic interventions, and to augment the ‘power of maybes’ as a space of anti-production, and resisting reduction (Ito 2019).