Lifelong learning as an individual activity that spans over one's life is not a reality yet, despite the general guides of educational policy. Especially the elderly, those over 65 years, are in danger of lagging behind. The solid trust in one's own activity and learning skills is required, besides, many aged today lack the learning culture (Tikkanen, 2003, Gerontologia, Helsinki: Duodecim). In step with an increasing elderly population, more attention needs to be paid on proper old age education technology, pedagogy, motivation, and needs. This chapter presents the experience gained from guiding elderly into the use of computers and Internet from three contexts. In addition, the chapter presents principles from literature on old age education based on cognitive aging (compensating and supporting the deficiencies and strengths) not forgetting the impact of empowerment by current ICTs in the life of elderly people. First, directing computer clubs for the elderly is demonstrated based on a WWW-questionnaire, as well as observations made during years 2007-2008 in Pieksämäki, Finland, and from Seniors' Club. Second, we show experiences from courses and home teaching for elderly. Finally, we discuss these forms of learning in two models: Chaffin-Harlow model of cognitive learning (Chaffin & Harlow, 2005, Educational Gerontology) and TUP-model for the contextual factors (Bednarik, Gerdt, Miraftabi, & Tukiainen, 2004, Proceedings of the ICALT 2004, that is to say from the learner's vantage point and that of the real-world context where learning takes place. The results show that the learning program for the elderly is strongly facilitated by peer support which is experienced during informal club-based activities, as well as having a jointly planned content which is tailored to their needs, motivation, and ability.M. Naumanen (B)