► Examines the factors affecting older adult adoption of digital technology. ► Reports on two case studies of older adults learning to use digital touchscreen tablet devices. ► Proposes models of older user technology acceptance from ease-of-learning, and system & user perspectives. This paper examines the factors and theoretical frameworks for the adoption of technology for older adults, and proposes two models of technology acceptance and rejection, one from an ease of learning perspective, and one from a system and user perspective. Both models are supported from reports on two case studies of older adults using handheld touchscreen tablet devices; one in which the participants are supported during tasks primarily related to walking and navigation, and one in which participants are unsupported in communication related tasks. The first study shows the powerful role that facilitating conditions have for learning how to use digital technologies for this user group, whether supporting through step by step guidance, providing a friendly space to use trial and error methods, and/or provision of a manual. The second study shows the pitfalls of a lack of facilitating conditions during initial use, and highlights potential for appropriate design in helping to avoid some user errors during this phase.