Assessment and the documentation of learning is an international issue in early childhood education (ECE) and has increasingly become a way for governments to exercise direct control over the practitioners working with young children. This paper details recent statutory guidance about assessment and documentation for English ECE settings and deconstructs the latest English ECE policies, highlighting that these often give contradictory messages to practitioners. It suggests that practitioners are caught up in playing a game: trying to make compatible assessment practices that address both the scientific discourse of empiricism and a more recent internationally influenced sociocultural discourse, as outlined by Soler and Miller. However, we concede that it is unrealistic to reproduce practices that have deeply culturally embedded significance elsewhere. The paper therefore outlines key challenges for English practitioners: how to use documentation as a generative assessment tool and how to make assessment more collaborative. We suggest that addressing these issues through building pedagogical knowledge could enable practitioners to develop greater confidence when playing the assessment game.