The rapid development of digital technologies and their increasing application in many areas of everyday life challenge all citizens to continuously learn digital skills. This also applies to older adults, among whom digital literacy is on average less well-developed than among younger adults. This article investigates why retired older adults participate in opportunities to learn digital skills. Multiple case design with both qualitative and quantitative methods was used to include the views of older adults from Austria, Finland, and Germany. The results of this interdisciplinary study indicated individual, social and technical reasons for their participation in digital skills training. Practical implications and recommendations for future studies are suggested.