Age-friendly initiatives are increasingly promoted as a policy solution to healthy aging, The primary objective of this article was to examine older adults’ and key stakeholders’ perceptions of the factors that either help or hinder a community from becoming age-friendly in the context of rural Manitoba, a Canadian prairie province. Twenty-four older adults and 17 key informants completed a qualitative interview. The findings show that contextual factors including size, location, demographic composition, ability to secure investments, and leadership influence rural communities’ ability to become age-friendly. Government must consider the challenges these communities face in becoming more age-friendly and develop strategies to support communities.