Innovation is a key component in trying new solutions for the students to learn efficiently and in ways that correspond to their own experience, where chatbots are one of these new solutions. One of the main problem that chatbots face today is to mimic human language, where they try to find the best answer to an input, which is not how a human conversation usually works, rather taking into account the previous messages and building onto them. Extreme programming methodology was chosen to use integrate ChatterBot, Pyside2, web scraping and Tampermonkey into Blackboard as a test case. Problems occurred with the bot and more training was needed for the bot to work perfectly, but the integration and web scraping worked, giving us a chatbot that was able to talk with. We showed the plausibility of integrating an AI bot in an educational setting.