This article reports a long-term ethnographic study on jamming and learning from an entwined artistic and educational perspective. The study investigates aspects of learning during a professional band's jamming and recording eight groove-jazz frameworks and a series of subsequent concerts with pre-academy students "sitting in." Fieldwork was documented through sound recordings, diaries, and field notes from participant observation and informal interviews. Analyses apply a situated learning theoretical perspective on the band members' as well as the students' participation and reveal important learning to take place. Analyses also indicate the musicians' changing participation being analytically inseparable from the changing music itself. The study's final argument is two-fold: Revitalising jamming as a studio-recording practice within popular music highlights important aspects of professional musicians' interactive communication processes. And transferring this artistic endeavour into an educational practice suggests an increased focus on students 'sitting in' with professional bands, and teachers playing alongside with students.