This paper argues for the foregrounding of improvisation and education "in the moment" within youth workers' professional development. Devised in collaboration with third-year Youth and Community Work students and lecturers at a university in Birmingham, this participatory action research project drew on work of jazz ethnomusicologists and educationalists that details the extensive preparation involved in acquiring the ability to improvise within jazz in order to counter the misconception of youth work as educational practice "on the wing". Through analysis of students' reflective writing, lecturer feedback, interviews with lecturers and video footage of students leading improvised dialogues with their peers, the study sheds light on the challenges and possibilities involved in the teaching and assessment of improvisation in youth work and suggests that students can be encouraged to actively structure their awareness of improvisation and take responsibility for developing a disposition towards it. The author argues that this is important, not only because such improvised practice "works" instrumentally in terms of engaging young people, many of whom are disengaged from formal education, but because it is also closely aligned ideologically with the value-driven purpose of youth work.