Abstract: This work describes an automatic news chatbot that draws content from a diverse set of news articles and creates conversations with a user about the news. Key components of the system include the automatic organization of news articles into topical chatrooms, integration of automatically generated questions into the conversation, and a novel method for choosing which questions to present which avoids repetitive suggestions. We describe the algorithmic framework and present the results of a usability study that shows that news readers using the system successfully engage in multi-turn conversations about specific news stories.