This study examines the effectiveness of a custom-designed chatbot in a blended learning environment, focusing on its adherence to instructional guidelines and its impact on student engagement. The chatbot was designed to prompt students with questions about concepts related to various academic majors, encourage elaboration on their responses, and provide tailored recommendations based on students' strengths. Results indicate that while the chatbot effectively engaged students in discussions, as students who received recommendations were likely to follow up on their topics of interest, it struggled to cover all topics of academic majors equally. The chatbot's efforts to encourage more detailed responses occasionally led to disengagement, with some students halting midway. These findings contribute to the growing research on chatbots as practical tools in real-world educational settings. Future research should focus on streamlining chatbot tasks, integrating student preferences to enhance engagement, and designing cohesive learning experiences that connect in-class and online interactions to improve the chatbot's effectiveness in academic advising and career guidance.