In this study, we explored the ways in which listening tools within technology-mediated environments can facilitate children's self-regulation of instrumental music learning between lessons. This interpretive multiple case study utilized a software application assigned for 22 weeks to a piano teacher and four students (ages 8-10). Data sources include student and teacher semistructured interviews and practice session observations. Self-regulated learning theory informed the recommended learning approach with technology and provided a lens for within- and cross-case thematic analysis. Study findings suggest that digital tools that provide accessible and customizable listening experiences can be used strategically to promote independent listening opportunities between lessons, in turn facilitating processes of aural familiarity and problem-solving. However, students' self-regulatory development was also dependent on learning preferences and sustained teacher facilitation. The recommendations in this study can inform instrumental teachers about pedagogical approaches with technology, and the implications can contribute to the design of digital environments to support children's instrumental learning.