How do academic advisors encourage students to consider the meaning, value, and logic of their educational journeys during appointments despite pressures from students and others to discuss rote information, such as curricular rules and requirements? The concept of stealth advising describes how advisors manage such pressures by weaving novel content into conversations without disrupting conversational flow or sacrificing rapport. Drawing on observations of appointments and interviews with students and their advisors, I discuss three stealth advising strategies: checking in on students' experiences, supplementing rote information with related content, and challenging or questioning students' decisions. I outline the challenges and limitations of using stealth advising to achieve quality advising.