This chapter address how technology enables people to augment aspects of, blur boundaries between, and connect across musical experiences in ways that might expand conceptions of musicality, musicianship, and who might be considered a musician. The chapter proposes three such approaches to leveraging technology: augmenting music and musical engagement, augmenting musical sharing and concert experiences, and augmenting performing and ensembles. These three approaches to augmenting music teaching and learning through technology and digital media have potential to expand how music educators and their students conceptualize and enact musicianship. The chapter forwards a perspective that leveraging technology and digital media to augment music and musical engagement situates the act of connecting and identifying musical relationships as a form of musicianship and way of being a musician.