This chapter reflect on the author's experiences as the local partner lead for two University of Leeds-led projects. It explores what can be understood from them about the relationship between communities, digital heritage archives, institutions, and heritage engagement. Heritage (hi)stories, digital skills enhancement, and community empowerment are frequently cited ingredients in the mix of approaches to promoting community regeneration and development. Between October 2014 and March 2015, the two projects explored some of these themes with residents of the Isle of Bute, Scotland. Jointly, the projects brought together community, academic, institutional, and private sector partners to create new digital tools to support heritage-based community research and creative expression, and to further explore questions about heritage perception and digital engagement. Thus, this chapter discusses the meaningful contribution that projects such as Pararchive can make in the wider context of national ambitions for digitally engaged communities, and how project implementation might usefully be aligned with local communities in the future.