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The rise of online learning brings convenience, but often lacks student engagement due to the absence of immediate support from peers or teachers. This study explores the use of chatbots to enhance online learning through a mixed-methods multiple case study involving two courses in information management (41 students) and English listening (46 students). We developed a chatbot Learning Buddy based on the Community of Inquiry framework (social, cognitive, and teaching presences) to guide and interact with the students. We measured student engagement and perceptions using quantitative and qualitative data. Results show students’ sustained engagement and positive perceptions of the chatbot. We will discuss effective chatbot-supported online learning design strategies based on our findings.