Public education is a cornerstone of our democracy and social advancement. However, current Vermont graduation rates would indicate that public education at the high school level does not address the needs of all twenty-first century learners. Research has revealed that personalization and creating a connected environment are promising innovations for improving education for all students. One structure that supports personalization, high school advisory, provides each student with an adult advisor that knows them well through their high school years. This research on high school advisory in Vermont was divided in two phases: 1) an assessment of the current state of advisory in all Vermont public high schools, and 2) a qualitative study that focused on the perceptions of students, advisors and administrators in 4 Vermont high schools with established advisory programs. In the second phase, a phenomenological framework was used to examine the perceptions of how advisory impacted academics, connectedness and the personalization of the high school experience. Document review, focus forum groups and interviews with the sixteen students, eight advisors and four administrators were conducted over a six-month period. Findings demonstrated that 53 out of 62 high schools in Vermont had some form of advisory program. In the study of four schools, over two-thirds of the students perceived that their high school advisory positively impacted their academic achievement. Advisors and administrators were less clear about the impact, however. Furthermore student-to-student connectedness was described positively by three-quarters of the students. The connection between advisory and personalization of education was the least clear both among students and advisors. All administrators and three-quarters of the advisors felt that in the future, personalization would become an integral part of the advisory program with the advent of Vermont Act 77, the 2013 legislation that mandates personalized learning plans and multiple pathways to graduation. Finally, there was considerable agreement in three schools that a significant roadblock to implementing effective advisories was a lack of support for advisory in the following areas: purpose, time, training and materials.