This chapter explores the relationship of theory to practice along with the political and pedagogical dimensions of the annual Creative Pedagogies Summer School, held at Bethlehem University in the West Bank, Palestine. The Summer School has been accredited as part of the MA in Creative Pedagogies and Community Practices, offering students a space to develop and apply arts-based research (ABR) approaches to articulate and address challenges within their diverse teaching contexts. Such approaches have historically been constrained by the Ministry of Education and Higher Education (MoEHE) which like many other Ministries of Education around the world, such as the UK, have focused predominantly on curriculum content and resource provision, rather than critical thinking or the creative pedagogical development of educators. While our previous research has focused on student perceptions of critical creativity (Adams et al., 2020), this chapter turns to the perspectives of the core team of six tutors, from Palestine, the UK and Finland, involved in the design and delivery of the Summer School. The programme prepares community-based educators, inclusive of youth workers, for critically engaged and contextually responsive practice in both formal and non-formal educational settings. It offers an immersive experience that integrates creative pedagogies with ABR methods, encouraging both tutors and students to interrogate their assumptions about learning through making, reflection and dialogue. Our account exposes some of the barriers that arise from the conditions in which the programme takes place, including the ongoing occupation of Palestine, as well as the possibilities for resistance against all attempts to restrict the creative act of reimagining education.