Accessibility Advocate AI is an innovative, always-available system designed to empower teens with hearing loss by helping them navigate local services and strengthen their ability to communicate effectively with their support network. Our goal is to improve user agency, empowering teens by helping them understand their unique needs and leverage available resources to thrive in any situation. When users encounter a new challenge or opportunity - referred to as a Situation - Accessibility Advocate AI steps in to provide tailored guidance. The system suggests actionable steps for utilizing local services, engaging with their support network, and organizing structured documentation to facilitate collaborative decision-making with trusted individuals. The system begins by gathering essential details through a comprehensive intake process. Users complete an intake form with basic profile information and can deepen this understanding by using the "Get To Know Me" feature. This feature enables the AI to ask insightful questions, building a nuanced understanding of the user's condition, needs, and communication preferences. This personalized approach ensures that every interaction is meaningful, adaptive, and user-centric. Accessibility Advocate AI emphasizes privacy and control, allowing users to export selected data in structured formats. This capability supports teens in sharing relevant information with members of their support system, making it easier to advocate for their needs. As a fully human-in-the-loop system, Accessibility Advocate AI prioritizes collaboration and user autonomy. It is not only a tool but also a trusted partner that adapts to the user's evolving circumstances, so that they have the reliable support they need to navigate life's challenges confidently.