Many studies on social interaction have used the humanoid robot NAO. In the present paper, we described our project designed to address the growing unmet need for alternative approaches to slowing the progression of cognitive decline in Mild Cognitive Impairment patients. NAO is the experimental platform used in an ecological setting: a center for the treatment of cognitive disorders and dementia of the Italian health service. This paper describes the study addressed to evaluate the effectiveness of human–robot interaction to reinforce therapeutic behavior and treatments adherence and presents the latest findings of functional tests and users investigation recently conducted. The robot was programmed to implement some tasks from the usual memory-training program protocol. In different training conditions, subjects participated in sessions with the support of NAO or only from the psychologist while the interaction was recorded for subsequent exploration. Data indicated that memory training with NAO resulted in an increase of visual gaze from patients and reinforce of therapeutic behavior reducing, in some cases, depressive symptoms. Unexpectedly, significant changes in prose memory and verbal fluency measures were detected. These findings suggest that further research on robotics in ecological settings is necessary to determine the extent to which they can effectively support clinical practice.