In the therapeutic void created by over 20 failed Alzheimer’s disease drugs during the past decade, a new marketplace of “brain fitness” technology products has emerged. Ranging from video games and computer software to mobile phone apps and hand-held devices, these commercial products promise to maintain and enhance the memory, concentration, visual and spatial skills, verbal recall, and executive functions of individual users. It is instructive to view these products as sociocultural objects deeply imbued with the values and ideologies of our age; consequently, this article offers a critique of the brain fitness technology marketplace while identifying limitations in the capacity of commercial products to realistically improve cognitive health. A broader conception of brain health is presented, going beyond the reductionism of the commercial brain fitness marketplace and asking how our most proximate relationships and local communities can play a role in supporting cognitive and psychosocial well-being. This vision is grounded in recent experiences at The Intergenerational School in Cleveland, OH, a multigenerational community-oriented learning environment that is implementing brain fitness technology in novel ways.