A large number of people in China suffer from chronic diseases and need to take medication for extended periods of time. To avoid taking medication repeatedly and incorrectly, pill boxes that have been designed to support correct usage are an essential need. This paper focuses on the user experience of pill boxes, using Norman’s three-level theoretical framework of Emotional Design as a guide. The design of my own innovative pill box and app was informed this framework as well as by an analysis of my own daily experience and behavior patterns of taking medicine, and comparisons with competing products in the market to extract design pain points and considerations. The pill box is designed in the shape of a bamboo tube and contains two parts, a timer and seven boxes, which are magnetically attached to each other. When the set time comes, the indicator and buzzer will be activated and the corresponding pill box will fall down, requiring the user to take the medicines and return it to its place. Users can manage medications, set reminders, change the status of the boxes and view medication taking records on the app. This uniquely design aims to balance utility and consistency with a playful sensibility and aesthetic to reduce stigma and encourage belonging.