Successful aging and active aging policies frame independence in old age as an expectation and a virtue in opposition to the once desired reciprocity between generations. Due to digitalization trends worldwide, mastering digital skills becomes another responsibility for older adults to remain independent. However, this process can create new forms of dependency as support from skilled users – usually the younger generation – is crucial for technology adoption among older adults. This study addresses how older adults may experience digital dependency as a personal failure and a burden upon younger generations. We conducted long-term ethnography among older adults adopting new technology in Brazil and Chile, countries with rapidly aging populations that have implemented aggressive digitalization strategies. The fast digitalization of public services may increase the risks of social exclusion for older adults as the less connected and less skilled age group in Latin America. Contrary to expectations suggested by the research literature, participants preferred to enroll in smartphone workshops instead of relying on their children. We volunteered in smartphone workshops for older adults and mapped the difficulties they face when adopting new technologies and the strategies they develop afterward to use technology while avoiding dependency. Participants may restrict their use of smartphones due to their limited digital skills or claim a lack of interest in technology as a self-defense strategy against appearing ignorant or incompetent. We found that participants preferred relying on friends for support instead, perceiving their help as a form of peer collaboration.