The field of music education has witnessed a surge of studies centering on informal learning practices in the past decade, many of which focus on the increasing influence of technology-dependent musics such as dance, rap, and rock. Paralleling this trend has been the digital democratization of recording technology, which has facilitated the music education of multitudes via music-making experiences with digital audio workstations (DAWs) such as GarageBand, Logic, Pro Tools, and Ableton Live. Drawing on ethnographic data including participant-filmed videos, screen recordings, and semi-structured interviews, this paper disseminates the findings pertaining to self-led learning strategies with DAWs. Highlighting the characteristics of Web 2.0 or Gen Y learners, the participants exhibited a preference for trial-and-error approaches by eschewing manuals and embracing the familiar action of clicking to evaluate the resulting consequence and relying on the ability to undo actions.