Art education commonly takes place in venues such as schools, art studios, cultural centers and art museums. Contexts have a direct bearing on what kind of program is proposed. The actors involved in art teaching also significantly determine objectives and strategies within institutional backdrops housing the artmaking. Of particular interest here are unusual contexts, when artwork is produced in confinement, i.e. psychiatric institutions, special education facilities, prisons, refugee and concentration camps. Several questions ensue: Who are the teachers/artists involved in engaging others in art within highly restricted environments? How does artmaking happen behind-the-scenes? What about materials? What do images say about individual subjectivities, and how do they help process the extreme conditions that imprisonment imposes? How does artmaking contribute to emancipation? This paper is part of a larger study focusing on artwork produced by political prisoners in paulista political prisons (in São Paulo, Brazil) (1969-1979) by bringing to the foreground information on the experience of artmaking at Terezín (Theresienstadt Ghetto) supervised by artist/art teacher Freidl Dicker-Brandeis. Studies of artwork produced in psychiatric facilities in the 1940s and 1950s (Author, year-a; Author, year-b) contribute to the present discussion, along with a current project under my supervision about the collection from the paulista political prisons during the military dictatorship (1964-1985). About the context: Theresienstadt was not a typical concentration camp–rather, it was established in 1941 as a ghetto/transit camp from which prisoners were deported to Auschwitz for extermination (Arendt, 2000; Kasperová, 2013). It was used to showcase to the Red Cross what Nazis purported to be ‘humane’ treatment. Though formal schooling was prohibited, several adult prisoners assumed the task of preparing children for living in freedom at a future time. They taught traditional Jewish values, using modern educational approaches that respected the diversity of backgrounds at the ghetto. Despite the bleak conditions of life at Terezín, children and youth were also involved in cultural activities (music, theater and visual arts), allowing “inmates to forget the horrors of the surrounding world” (Kasperová, 2013, p. 52), while maintaining a semblance of normal life and learning. Dicker-Brandeis, born in Viena in 1898, was an art teacher sent to Terezín in December 1942, with her husband Pavel (Hurwitz, 1988). Before deportation and extermination at Auschwitz in 1944, she managed to hide two suitcases stuffed full of drawings, paintings and collages by boy and girl prisoners. Articles by Leshnoff (2006), Wix (2010), Pariser (2008), Hurwitz (1988) were instrumental in presenting biographical information on Dicker-Brandeis’ life and accomplishments. Other texts focus on the artworks themselves (Golomb, 1992) and on cultural and educational initiatives that took place at Terezín (Peschel, 2012; Leschnoff, 2006). Along with reproductions of the children’s artwork, the literature produced about experiences of artmaking at Terezín enables us to establish connections relating the ghetto experience to artmaking in other contexts of confinement, so as to understand how art teaching can contribute to emancipation of the imagination.