In this session, we will focus on what faculty can support with AI, what students actually do with AI tools, and what their use can teach us about learning and teaching. Especially, we will share over two years of cross-school experience designing and implementing a course-based AI teaching assistant across multiple disciplines and student populations. Drawing on real usage data from faculty and students, community of practice throughout the years while using the bot, and instructional design reflections, the session examines the kinds of questions students ask AI over time, as well as faculty experiences of using the bot to support students. Rather than positioning AI as a replacement for instruction or as a means of finding accurate solutions, this session reframes AI as an important assistant to the learning process, as faculty and students seek clarity, struggle with concepts, and need additional scaffolding. Participants will understand the reality of benefits and challenges of using internal coursebot AI, instructional choices, and student support strategies, while maintaining a human-centered and responsible approach to teaching with AI. Attendees will leave with practical insights on using AI tools, including strategies for leveraging custom AI and the internally built coursebot, and a strategy for using AI tools intentionally and purposefully.Keywords:#TeachingWithAI #VirtualCourseBot #HumanCenteredAI