The tensions present in learning jazz improvisation are well recognized given the contextual shift from more informal environments such as jam sessions and apprenticeships towards academic settings such as school bands and college jazz programs. Research suggests that the development of instruction in music education be informed by and modeled after expert practitioners, yet scant evidence exists on the most effective strategies, methods, and/or approaches for teaching jazz improvisation, in particular against the backdrop of this shift in educational paradigms. In response, the purpose of this phenomenological study was to investigate seven jazz educators' lived experiences teaching jazz improvisation. Seven expert jazz educators situated in a variety of teaching contexts throughout Northern California were recruited using purposeful, snowball sampling strategies. Data were collected through semi-structured interviews, observations of the participants in a teaching context, and documents such as syllabi, handouts, and recordings. Five themes in the form of vignettes describe these participants' common experiences in teaching jazz improvisation: (1) Teacher as Guide; (2) Teacher as Motivator; (3) Psychological Aspects; (4) Navigating the Academic Chasm; and (5) Cultivating Lifelong Learners. Implications for practice and suggestions for future research are discussed.