Most related research about intra-family communication follows the reality of developed countries, where older adults can live independently from their families and are likely to embrace technology. Contrarily, in Chile and other Latin American countries, most older adults live close to their families, are usually dependent of the latter, and rarely use digital means to communicate. Through cross-generational interviews, we identified attitudes, agreements, and expectations that describe how middle class Chilean families, living in urban settlements, interact with their elders. The study findings indicate that the approach used by the adult children to take care of their parents produces a vicious circle that stresses out the former and limits the technology adoption of the latter. Therefore, new ways of interacting with the elderly are required and digital technology has the potential to produce this change.