In this article, we begin by briefly reviewing some of the national statistics on older adults and computer usage, statistics that led each of us to volunteer as teachers to develop technological literacy programs for older adults at local community centers. Because we recognize that all literacies are developed and used by specific people in specific contexts, we describe the community centers where we volunteered (New England and the Midwest), our roles as teachers and later as researchers, the older adults with whom we worked, and the technological literacy curricula we developed and then revised based on extensive input from participants. Drawing from our experiences and from qualitative, interview-based research with participants, we seek in this article to discuss the barriers and benefits to older adults' acquisition of technological literacies. In particular, we argue for the importance of building communities of practice based on relational support and interaction and for the importance of drawing from assets and needs existing within communities. (Contains 10 endnotes.)