This case study in UbiComp technology and design presents a "Playful Toothbrush" system for assisting parents and teachers to motivate kindergarten children to learn proper and thorough brushing skills. The system includes a vision-based motion tracker that recognizes different tooth brushing strokes and a tooth brushing game in which the child cleans a virtual, mirror picture of his/her dirty teeth by physically brushing his/her own teeth. The user study results suggest that Playful Toothbrush enhances the effectiveness of kindergarten children in brushing their teeth, as measured by number of brushing strokes, duration of brushing and thoroughness of teeth cleaning. Author Keywords Ubiquitous computing, occupational therapy, persuasive technology, children, tooth brushing. ACM Classification Keywords H5.2. Information interfaces and presentation (e.g., HCI): User Interfaces.