In this article I reflect on my experiences as a previously incarcerated individual being involved in theatre performance for the first time. I reflect on how my involvement in arts and education programmes in prison made me aware of the larger structures of Whiteness that were embedded in the educational and arts contexts that I found myself in later in life. I argue that much of the arts programming and delivery supports rather than challenges structural forces of White supremacy and domination that underpin both the prison system and educational institutions in the US.