(1) Background: The RESILIEN-T system addresses the need for innovative solutions to support self-management in older people with Mild Cognitive Impairment (MCI). Despite the increasing prevalence of dementia and MCI, there is a lack of tailored solutions for these individuals. The RESILIEN-T system aims to empower and engage people with cognitive decline by providing a modular platform for self-management and coaching services. (2) Methods: Italian data collected for the RESILIEN-T project involved 62 older participants randomly assigned to the intervention or control group. Data were collected through questionnaires and user interactions with the system over a three-month period. (3) Results: Quantitative outcomes showed no significant differences between the intervention and control groups, except for an improvement in perceived memory capability in the intervention group. The usability assessment indicated a high level of acceptance of the RESILIEN-T system. (4) Discussions: Although no significant improvements were observed in most quantitative measures, the high user engagement and acceptance suggest the potential effectiveness of the RESILIEN-T system. Future improvements could involve integrating smart objects and interactive virtual agents. Overall, RESILIEN-T represents a promising step toward empowering individuals with cognitive impairment in their self-management and decision-making processes.