It is expected that, by 2050, people aged over 60 in 65 nations will constitute 30% of the total population. Healthy aging is at the top of the world political agenda as a possible means for hindering the collapse of care systems. How can ICT/sensing technology meet older people’s needs for active and healthy aging? This qualitative study carried out in Italy and Romania in 2020 involved 30 participants: older adults, caregivers, and stakeholders. Based on a user-centered design approach, this study aimed to understand which requirements of ICT/sensing technologies could match people’s needs of active and healthy aging. Findings highlighted that ICT/sensing technology needs to focus on six major themes: (1) learnability, (2) security, (3) independence, empowerment, and coaching values, (4) social isolation, (5) impact of habit, culture, and education variables, and (6) personalized solutions. These themes are consistent with the Active Aging framework and the factors that influence perceived usefulness and potential benefits among older adults. Consequently, this study shows how well-known, but still unresolved, issues affect the field of information and communication technologies (ICTs) to promote active and healthy aging. This suggests that the reinforcement of the public health system, especially considering the pandemic effect, requires a concrete and formidable effort from an interdisciplinary research network.