The use of music technology in the enhancement of young pianists’ musical improvisations has been scarcely explored in instrumental music teaching and learning research. In the present study, 19 piano pupils aged 6–10 from the UK and Greece used an interactive improvisation system called Musical Interaction Relying On Reflexion (MIROR)-Impro for six weeks in order to enhance their improvisational skills. This system engages pupils in a musical dialogue, answering in the same style as the pupil’s input, creating a reflection of the user’s own musical ideas. Children participating in the study were drawn from a notation-based and classical piano education background, and had various levels of piano expertise. Four case studies are presented here in detail. Results indicate that the system enhances young pianists’ capability musically to explore and improvise, and several further questions are raised regarding the possible ways the system can be used in practice in the piano lesson.