Osteoporosis is a common musculoskeletal disease with no cure, with an estimated 400,000 patients in Hong Kong. Unfortunately, an accurate prognostic tool is lacking given that its precise etiology remains unknown. It is often regarded as a ‘silent disease’ since research has estimated that about 75% of the cases are still undiagnosed or are diagnosed only when a bone fracture occurs. Coupled with the lack of patient self-management support to both the patient and their caregivers, this flawed disease management leads to poor treatment outcomes for osteoporosis patients. In light of these detrimental consequences and the aging population, we develop a state-of-the-art AI-powered osteoporosis prognostic system to enable mass screening in the community by analyzing easily accessible predictors from patient characteristics and clinical data. To imbue osteoporosis patients with the mentality of wellness proactivity as opposed to illness reactivity, the self-management mobile application follows international clinical guidelines closely to provide regular intelligible health information and personalized education, for instance, lifestyle modifications, pain management, and exercise suggestions. We also provide more objective functional capability measurement via our in-app AI-powered gait video analysis. It allows users such as clinical practitioners and their caregivers to enjoy cost-effective and continuous functional outcome assessment.