Working with a large multidisciplinary team, including computer scientists from the Centre for Advanced Computing at Queen’s University, a dedicated team from IBM, and post-doctoral fellows for the Centre for Health Services and Policy Research at Queen’s, the research team created a prototype ‘chatbot’ to assist military Veterans and their families to self-manage important mental health problems via web and, ultimately, smart phone applications. Key motivations behind this project were to help minimize stigma through anonymous conversations, support mental wellness through self-management, and promote help-seeking, when appropriate. The research team conducted numerous interviews with end-users to learn the unique vernacular used by military personnel and family members to describe mental health concerns. The chatbot was equipped with IBM Waston’s natural language processing to pick up sentiment, analytics, tone and conversation, using these to interpret problems and direct the user into specific conversational streams designed to assess depression, anxiety and PTSD. Afterwards, depending on the content shared, the conversation could be fluid and iterative across the different streams. The user has several options, such as chatting, completing a screen to identify the severity of symptoms, going directly to tip sheets, or finding a mental health professional in their area.