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This paper describes a pilot application developed by the authors within a project in the area of elders assistance. Specifically, the work addresses the problem of assigning scheduled activities to a set of volunteers by means of an interactive tool that considers both users’ needs/preferences and constraints posed by the organization that manages the volunteers. Particular emphasis is given to the problem of assigning a group of seniors to the “right task” so as to obtain a positive outcome of the services offered by the volunteering association while maximizing the volunteers’ level of satisfaction perceived, in this domain, as a relevant requirement. This paper describes the design of a complete application for supporting this process focusing, in particular, on the back-end functionalities where a formalization as a generic optimization problem and a heuristic, developed to serve the time constants required in …