Drawing on convention theory and sociology of critique, this article examines how teachers at a Swedish folk high school coordinate students' activities through tests. Through ethnographic descriptions of exercises, assignments, presentations, and exhibitions that test students' engagement, it is shown how the teachers seek to depart from the standardized assessment procedure associated with formalized schooling. More specifically, the teachers' tests destabilize the prevailing understanding of what art "is," support the students to collectively explore and experiment with materials and highlight promising dimensions in their art-making. The article highlights "what is at stake" in art education and recognizes certain conventions as central in formatting, confirming, and interrogating the students' understanding of their artistic practices. Through these tests, students face a contradiction of freedom: the freedom to find their unique voice and follow their inner calling, versus the explicit and imposed expectation to express their freedom in a certain way.