This paper explores the relationship between design logic and reasoning and the methodological and epistemological positioning of design-based knowledge production. Examining the relevant literature, we propose that the naturalistic logic of the American pragmatist philosopher John Dewey offers a potentially useful contextualisation of how logic, reasoning, method and, ultimately, knowledge can be understood as arising from, and be responsive to, context. This is considered in relation to the long-term delivery of a design research programme—termed Experience Labs—which was seen to undergo a gradual methodological shift in response to contextual concerns. It is our core argument that Dewey's logic can function as a valuable theoretical device, mediating between design and the necessity of methodological and epistemological explication in research.