Despite widespread digitalization, certain marginal and societal groups can still encounter challenges in the digital world. Promoting digital inclusion and digital support aims to reduce these disparities and enable equal participation. In this article, we examine the quality and dynamics of informal learning and digital support provided by warm experts from the perspective of older adults' subjective experiences. Specifically, we ask (1) what are the key elements of informal learning in the context of older adults' acquisition of digital skills? Based on the first question, we further examine (2) how do the identified key elements of informal learning influence older adults' subjective learning experiences and independent use of digital technologies? Our inductive thematic analysis is based on participant-induced elicitation (PIE) interviews (n = 21), conducted with older adults (aged 65+) in Finland in 2018. Our findings suggest that older adults are a heterogeneous group with different support needs and diverse prior experiences with digital technologies. Even when digital support from friends and family is available, it does not always facilitate independent use or meaningful learning experiences. The results show how informal digital support provided by warm experts can not only enhance, but also hinder digital inclusion and independent aging.