Older people, especially those living with dementia, experience significant barriers to meaningful participation in their communities. Focusing on the expansion of an arts-based program to address social inclusion for older people via information communication technology (ICT), this paper identifies the challenges and opportunities of the digital delivery of the Baycrest NBS Sharing Dance Seniors program, a weekly dance class professionally instructed via online-streamed video and facilitated in-person in community and institutional care settings. Findings are drawn from older people and career experiences in community-based, multi-method pilot studies in the Peterborough Region, Ontario, and the Westman Region, Manitoba (2017-19) Canada. Through observations, diaries, focus groups, and interviews featuring the experiences of program instructors, participants, carers, administrators, facilitators, and volunteers, the challenges and opportunities presented by the digital delivery of the Sharing Dance program are analyzed as they relate to understanding social connectivity and relational and multi-dimensional influences on social inclusion. Findings point to the key role of facilitators and in-person support, with implications for the development of social resources and facilitator training in community and institutional settings.