This chapter critically examines how community radio stations in South Africa are navigating digital transformation through two contrasting case studies: Hillbrow Radio, an urban, youth-led, online-only station serving a marginalised community, and Mbhashe FM, a rural broadcaster that transitioned from digital to FM broadcasting. Using Carpentier’s Access–Interaction–Participation (AIP) model and Gumucio-Dagron’s sustainability framework, the chapter explores how digital technologies are reshaping content production, community engagement, and social, institutional, and financial sustainability. Findings reveal that while digital platforms offer opportunities for expanded reach and interactivity, they also expose deep structural inequalities, particularly in rural areas. Hillbrow Radio exemplifies innovation and entrepreneurial adaptation, whereas Mbhashe FM illustrates the persistent infrastructural and financial challenges faced by rural community radio stations. Despite their differing contexts, both stations grapple with ensuring genuine community participation and long-term sustainability in an era marked by rapid technological change and regulatory confusion. The chapter argues for a redefinition of “community” in the digital age and underscores the need for inclusive, hybrid models that align digital innovation with local realities to ensure community radio remains a vital platform for marginalised voices in a converged media landscape.