The accelerated pace of digital innovations represents a challenge to some individuals, particularly for older people with low digital skills. Several studies focused on information and communication technologies (ICTs) education programs in institutional settings, yet the provision of informal support in the family context is a critical element in the digital literacy of older people. This study examines the familial intergenerational dynamics that facilitate or hinder the digital literacy of grandmothers and carries out a comparison in different cultural contexts. Focus groups were conducted with grandmothers aged 65 and over in Colombia, Italy, Peru, Romania and Spain, followed by thematic analysis. The results show that the grandmothers involved in the study acquire new digital skills through explicit and non-explicit learning dynamics. Grandmothers first resort to their children and grandchildren for explicit requirements, although facing various emotional and attitudinal challenges that hamper this learning. Otherwise, non-explicit learning dynamics emerge in their everyday interaction with offspring and include enactive, immersive, vicarious, and collaborative learning. Thus, intergenerational dynamics are key for grandmothers to keep updated with the continuous flux of innovations. Moreover, the explicit and non-explicit dynamics described should be considered in policies related to digital literacy of older women.