Background: The SoBeezy program is an innovative intervention aimed at promoting and fostering healthy aging and aging in place by proposing to older adults concrete solutions to face daily life, tackle loneliness, promote social participation, and reduce the digital divide, thanks to a specific, easy-to-use voice assistant (the BeeVA smart display). Objective: This study aims to assess the acceptability of the SoBeezy program and its voice assistant and to identify potential areas of improvement. Methods: A 12-month experimentation of the program was deployed in real-life conditions among older adults living in the community in 4 pilot cities of France. Launched during the first lockdown of the COVID-19 crisis, this multisite study aimed to assess acceptability using questionnaires and interviews conducted at baseline and at the end of the experimentation. In addition, a series of meetings were conducted with SoBeezy staff members to obtain direct feedback from the ground. Results: In total, 109 older individuals were equipped with BeeVA to use the SoBeezy program; of these, 32 (29.4%) left the experimentation before its end and 69 (63.3%) completed the final questionnaires. In total, 335 interventions were conducted and 27 (39%) of the participants requested services, mainly for supportive calls and visits and assistance with shopping, transportation, and crafting-gardening. Of the whole sample, 52 (75%) considered BeeVA as a reassuring presence, and few persons (15/69, 22%) reported a negative opinion about the program. Among the participants, the voice assistant appeared easy to use (n=57, 82%) and useful (n=53, 77%). They also were positive about the BeeVA smart display and the SoBeezy intervention. Conclusions: This multisite study conducted in real-life conditions among more than 100 older adults living in the community provides enlightening results of the reality from the ground of digital tools designed for the aging population. The COVID-19 context appeared both as an opportunity, given the massive needs of the older adults during this crisis, and as limiting due to sanitary constraints. Nevertheless, the experimentation showed overall good acceptability of the voice assistant and a high level of satisfaction of the participants among those who really used the system and could be a way of improving the autonomy and well-being of older adults and their families. However, the findings also highlighted resistance to change and difficulties for the users to ask for help. The experimentation also emphasized levers for next deployments and future research. The next step will be the experimentation of the activity-sharing component that could not be tested due to the COVID-19 context.