Complex systems like SMS benefit from dedicated AI Chatbots. Searching directions using keywords results in dozens of sets of long and often redundant directions and the keywords used in the search do not always pull the correct set of directions. AI chatbots can help find answers and provide links to further information very efficiently. It can customize responses as it learns the user's role in the district and how SMS is set up for them (e.g. a teacher using secondary or standards based grading). It could give suggestions of features the user didn't know to ask about and give feedback to Skyward so they know what users feel is most confusing.