Understanding language is hard; maintaining a dialogue/conversation is even harder- especially for computers. But in recent years, there’s been an immense boost in conversational AI, thanks to the emerging research of Machine Learning and Deep Learning techniques. In this talk, we’ll discuss the challenges in building dialogue systems & bots, the way ML and DL are used to improve Natural Language Understanding in products, and open-source Rasa. We’ll take a look at Lemonade’s chatbot technology, including a deep dive under the hood.