Purpose: The purpose of this paper is to examine how chatbots can be used to address two key struggles that students face in first year--a sense of being disconnected from the instructor, and information overload. The authors propose that chatbots can be a useful tool for helping students navigate the volumes of information that confront them as they begin attending university, while at the same time feeling somewhat personally connected with the instructor. This is achieved without increasing instructor time commitment, and perhaps reducing it in large classes. The paper reveals the results of applying this tool in a large first year class and proposes improvements for future iterations. Design/methodology/approach: A tool was designed and implemented and tested against research insights. Findings: Chatbots are an effective means to reduce student transition challenges. Research limitations/implications: Technology which feels social and personal as well as functioning on a tool that students use will make the student feel more connected to the course and the instructor. Practical implications: Tools aiding transition should be easy to use and allow customizable information access. Originality/value: Chatbots are an unexplored tool. They have the benefit of addressing information overload as well as making the student feel socially connected without increasing instructor workload.