Festivals have been credited with significant social effects: connecting people, developing audiences, linking emerging with established artists, even encouraging intercultural dialogue and participating in ongoing positive social change. At the same time, the concretization and commodification of Indigenous expressive culture is a risk in festivalized settings. Emerging from dialogue with Indigenous music industry professionals and musicians, this essay explores how music festivals that prioritize Indigenous leadership and attend to internally diverse audiences can strategically choose productive narratives for the groups they serve. While remote collaboration is not new, it became required during the COVID pandemic. With its focus on musician and audience development, the sākihiwē festival in Winnipeg, Canada demonstrates some of the ways in which First Nations, Métis, Inuit, and international Indigenous musicians are reaching audiences in challenging times. Possibilities for audience curation shift online, as do the tools available for listener engagement. Musicians continue to wrestle with questions of addressing stereotypes as well as how to inspire and educate audiences in a festival atmosphere. To these concerns, performers add the manner in which they work with streaming technology, develop professional mentorship with physically distant colleagues, and create connections with online listeners. As uncertainty continues around music festivals in the near future, this essay asks how possibilities are shifting around cultural and political change through music festival performance.