While extensive research has demonstrated the social, emotional, and cognitive benefits that may be associated with participatory music-making among older adults, there has been less attention paid to the actual tools (e.g., musical instruments, resources) that can provide a ‘way in’ to creative musical development in later life, and limited research has focused on the intersection between the pedagogies, tools, and contexts, and the ways in which those factors may influence creative or developmental outcomes. This chapter focuses on two community groups of novice adult music learners, where the aim was to identify the musical tools and the pedagogies that would support creative expression and musical development. The two groups used a range of instruments, including rock band instruments, percussion, and iPads, in activities that focused on learning musical concepts, creative improvisation and songwriting, and learning to perform well-loved songs. Both groups pivoted from in-person to online music-making during the global COVID-19 pandemic, when the iPads became a central tool. Data were collected through video recordings of the weekly offline music sessions, facilitator field notes, and through focus groups and interviews with group participants. The chapter will explore the following questions: