Global aging and increasing multimorbidity are questioning the sustainability of healthcare systems. Healthy aging is at the top of the world political agenda, as a possible means for hindering the collapse of care systems. In the aging process, the transition to retirement can lead to an improvement or a deterioration of physical and psychological health. Digital health coaching technology can support older adults at this stage, but what must be the role of such a solution in promoting healthy aging and shaping sustainable care? This qualitative study, carried out in Italy in 2019, involved 15 older workers, retirees, and colleagues. Based on a user-centered design approach, this study aims at gathering older adults’ feelings on a digital health coaching technology for exploring this solution’s potential in promoting healthy aging. Findings highlighted that the digital health coach may help older adults improve several health determinants, e.g., physical activity, cognitive capabilities, and social life, but it can also entail the risk of stigma and break people’s privacy. The latter can be guaranteed by technology customization and codesign. Further research on the digital health coach benefits to boost healthy aging is needed to understand its potential for shaping future sustainable healthcare.