The broader impact/commercial potential of this Small Business Innovation Research (SBIR) Phase I project is a novel chatbot that provides support to endometriosis patients. Endometriosis is a debilitating chronic pain disorder that impacts approximately one in ten women in the United States - resulting in significant loss of productivity, low quality of life, and greater than $80 billion annual economic burden. This artificial intelligence (AI) chatbot aims to conversationally educate users regarding clinically accepted paradigms of care and options during scenarios including painful endometriosis flare-ups. This project ultimately aims to improve patients' self-knowledge and quality of life, expand access to patients in rural communities to improve endometriosis patient recovery, and reduce the burden of the disease due to lack of knowledge or hesitancy for proper self-care.This Small Business Innovation Research (SBIR) Phase I project will develop an on-demand endometriosis flare-up management chatbot using advanced Natural Language Processing (NLP) and Understanding (NLU). Many endometriosis patients experience pain or symptoms on a daily basis but symptoms can become unbearable during flare-ups, causing patients with little support to seek emergency room care. The conversational chatbot will be trained to answer user?s questions, guide them through pain-reducing exercises such as pelvic floor therapy, and provide direction to professional resources. This framework uses an internal Natural Language Understanding unit to create user intents, variable entities, conversation context, and conversation resuming slot filling. The technology incorporates emotional understanding and empathetic mirroring allowing the chatbot to have a natural freeform text conversation with the user to encourage them to freely express themselves and feel understood during moments of crisis. This chatbot will serve as a digital companion for patients, acting as both a supportive friend (listening and validating) and as a virtual coach (guiding the patient through exercises to alleviate symptoms). This technology project will design, develop and validate the chatbot in a limited patient pilot.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.