Research, as knowledge production, is an ethico-political event. This assertion forms this chapter’s starting point for reconsidering and reconfiguring the epistemological, methodological and analytical framework for my doctoral research study into the dialectics of playwork. The original study was ethnographic, using Cultural Historical Activity Theory (CHAT). It argued that playwork’s fundamental contradiction was presented as that between understanding children’s play as autotelic and self-organising on the one hand, and on the other seeking and accounting for public funding that requires services to address policy agendas. Insights were drawn from moving to and fro between empirical data and literature not frequently used in playwork research. In this chapter, those insights are read through more recent engagements with literature to suggest that whilst traditional playwork theorising is invaluable, there is more that can be said about play from a playwork perspective. This seeking to disturb comfortable and common sense understandings of play is a political and ethical endeavour.