The concept warm experts originally referred to people who helped their friends and family to come to terms with home-based computers and Internet connections. As digital technologies have continuously come to permeate our everyday lives, the tasks for warm experts have grown in kinds and character. The present study contributes to our understanding of warm experts by exploring the learning process involving the warm expert and the less knowledgeable other(s). Drawing on interviews with older adults (70 to 94 years of age), the study specifically explores older users’ experiences of learning about digital media with children and grandchildren. The results reveal how interaction with warm experts constituted important learning opportunities for the older adults, in which they developed their skills in using digital media. However, establishing potential learning situations and learning from warm experts was not a straightforward matter, but surrounded by a multitude of barriers structuring the possibilities for learning. This shows how the role of the warm expert is fluid and materializes in different ways in different situations. The warm expert can take the position (or be positioned) as one who solves technical issues. The warm expert can be one who fails in teaching, or one who adopts the position as a warm teacher and contributes to learning among the less knowledgeable user. In order to also be a warm teacher, the warm expert needs to understand the specific learning needs and styles of the less knowledgeable other and adapt to these needs.