To engage in discussions of artwork meaning is to engage in critical reasoning, a factor that is central to the interpretation of artworks in the art classroom. While this may appear as a common-sense claim that reflects the tacit assumptions most art educators have about students' critical dispositions in art, it is also evident that little is known about the deeper structures underlying students' critical reasoning and how such structures shape students' interpretations of artworks. Drawing on my research on students' theories of critical meaning in art, this article explores the nature of practical and theoretical constraints on students' critical reasoning about the meaning of artworks. I account for how intentional beliefs, language and representational artefacts function as a nexus of real constraints that condition students' advance into interpretations of the social meaning of art. After briefly outlining the design and methodology of my study, I examine students' critical reasoning performances during the formative period of development between middle to late childhood. The findings reveal that with increasing age students gradually learn to exercise their own critical intentions and represent inferences that acknowledge the significance of constitutive rules and force of a collective intentionality in the artworld on their interpretations of artworks as artefacts. I then make some conclusions about the relationship of domain-specific shifts in art understanding, the role of intentionality, representational understanding, beliefs about art and reasoning skills to the linguistic, theoretical and artefactual constraints conditioning students' intuitive advance into real understandings of art.