This study describes the barriers and supportive factors for learning about and using Information and Communication Technologies (ICT) present during a learning intervention designed to enable older adults to use ICT for fostering healthy aging in terms of promoting functional ability. Forty-one adults, older than 60 years, participated in a blended learning environment to learn how to use ICT for supporting cognitive performance and social interaction. The classrooms sessions were video recorded, and the data were analyzed using an inductive process of content analysis. The main observed barriers for learning about and using ICT were lack of experience with ICT, negative emotions such as fear, and shame related to the learning process and restrictions for individual support. On the other hand, the main supportive factors for ICT learning were a collaborative learning environment, the motivation for becoming efficient and independent ICT users, and using learning strategies focused on supporting cognitive abilities and overcoming lack of experience with ICT. The most observed factors for overcoming the identified barriers included peer support, the motivation for using ICT independently, and the opportunities for practising the learned skills. Based on the results, the paper discusses some opportunities for improving the design and implementation of this type of learning interventions.