Academic advisors see it all the time--skills successfully applied by underclassman in high school are not working in college. This article describes how advisors can help struggling students in self-monitoring and self-regulating their study experiences using metacognitive development as an intervention. Metacognition development includes improvement of students' abilities to accurately sense whether they have or have not adequately learned something. Students' practice recognizing the difference between shallow thinking and deep thinking as well as misconceptions they may have pertaining to effective learning practices. The work of advising educators is geared towards helping students succeed and persist in college. Advisors do this in individual and group advising sessions, probationary and reinstated student contract requirements, study strategy workshops, developmental and first-year seminar courses, tutoring and learning center services. All programs are designed with methods to give students meaningful experiences that makes the difference between failure and success.