This column explores from a philosophical perspective how sound recording and media create a context different in consequential ways for music education. The author relates the story of his connection to his son through the ukulele in two ways: first, through playing and singing together; and second, through a recording of their music. These differences are explored through a pragmatic approach to technology, with a focus on three issues: commoditization, efficiency, and sound fidelity. The author then explores two different kinds of responses that educators might explore in thinking about music education contexts and media awareness: an approach to focal practices following Borgmann, and the technological transparency approach recommended by Dewey.