The widespread availability of Information and Communications Technology paradigms encourages people, especially older adults, to maintain independence in their daily activities, improving health and well-being. However, some elements of criticality can arise when trying to meet two worlds apart. The present work aims to discuss the main factors that affect older people’s engagement with a user-centred software platform to increase people’s awareness of the availability of services for social care and entertainment purposes. A mixed-method approach was defined to correlate the attitude towards technology, measured through the TechPH index, to the usability and user-experience outcomes. Despite the limited sample size, the findings of this preliminary study suggest that the use of technology is not associated with any increase in the stress level, since the initial perceived difficulty to learn and use the system decreased after some training. Moreover, education level, living conditions, age, gender and TechPH index do not affect the usability of the SW interface, rather it depends on the familiarity with the use of the smartphone, the perceived usefulness and the difficulty in using it. The requirements and recommendations gathered during the test will be used to optimize the SW interface design for better acceptability and usability by older adults.