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In this paper, we outline inherent tensions in Agile environments, which lead to paradoxes that Agile teams and organizations have to navigate. By taking a critical perspective on Agile frameworks and Agile organizational settings the authors are familiar with, we contribute an initial problematization of paradoxes for the Agile context. For instance, Agile teams face the continuous paradox of ‘doing Agile’ (= following an established Agile way of working) versus ‘being Agile’ (= changing an established Agile way of working). One of the paradoxes that organizations face is whether to start their Agile journey with a directed top-down (and therefore quite un-Agile) ‘big bang’ or to allow an emergent bottom-up transformation (which may be more in-line with the Agile spirit but perhaps not be able to overcome organizational inertia). Future research can draw on our initial problematization as a foundation for subsequent …