This research was motivated by a desire to help office workers change their sedentary behavior because a prolonged sedentary posture increases the risks of developing musculoskeletal injuries and chronic diseases, thus threatening their physical and psychological well-being. Regular breaks involving low-effort physical activities are effective in reducing the adverse impacts of inactive behaviors. In this article, we present the design of a posture-based interactive system called HealthSit, which was developed to promote a short lower-back stretching exercise during work breaks. Through a within-subject study involving 30 office workers, the effectiveness of HealthSit in facilitating the stretching exercise was examined by making comparisons between an interaction-aided, a guided, and a self-directed exercise mode. We also used HealthSit as a research probe to investigate the interactivity of the system in enhancing user experience and the psychological benefits of the fitness breaks. Compared with the other two modes, the interaction-aided exercise mode significantly improved the quality of the stretching exercise and enhanced motivation and emotional state. These results confirm the effectiveness of HealthSit in supporting fitness breaks as a new workplace technology. Based on our study, a set of design implications have been derived for technology-assisted fitness work breaks.