Students are often asked to reflect on community-engaged and other high-impact experiences—but what learning actually appears in those reflections? And what happens when responses stay surface-level or disconnected from intended outcomes? This meet-up explores an emerging AI-supported approach that guides reflection rather than simply collecting it. Through thoughtful follow-up questions, students move beyond generic responses while faculty shape reflection around their own learning goals and context. We’ll consider how technology can make reflection more intentional, aligned with learning objectives, and responsive to the experience itself.