Criticality is an important means to negotiate uncertainty, which has become a characteristic of teaching and learning conditions in postmodern times. This paper draws from an empirical comparative case study conducted in the uncertain discipline of fine art visual practice, where critical judgement and meta-cognition are important for professional contemporary art practice. Charting the curricula intended by staff and the culture experienced by students, the paper considers the relation between the espoused theory of criticality in two art schools and their theory-in-use within assessment structures and cultures. Emphasis is placed on the significance of such approaches to criticality for the student experience and their learning engagement. Emerging discourses of 'subjectivity' and a lack of development of student meta-cognition indicated that, at an undergraduate level of study, the curricula of these cases are unwittingly underpreparing their graduates for operating with agential criticality as they enter the uncertain context of contemporary art.