Research has shown that adolescent students' sense of connection to adults and peers and sense of belonging to school are important for academic achievement, social-emotional growth and well-being, and overall success at school. One key mechanism schools have implemented to foster such relationship building is advisory. Much of the advisory research has focused on advisory programming and best practices. While some scholarship has found advisory programs to improve students' sense of connectedness to their advisor and peers and to increase students sense of belongingness to their school, the advisory literature also indicates that a number of schools and educators have experienced challenges to making advisory work for them and their students. The purpose of this mixed-methods study is to explore how and to what extent enhanced advisory fosters ninth grade students' development, as characterized by the Five Cs of positive youth development. The sample was comprised of 55 ninth grade students participating in enhanced advisory (EA), seven EA advisors, and a previous cohort of 96 ninth grade students who participated in traditional advisory (TA). Pre-post surveys were used to measure the development of students in EA over the course of one academic year and end-of-year surveys were used to compare the positive development of students in EA to that of a previous cohort of ninth grade students in TA. Interviews with EA students and advisors were used to investigate and illuminate the quantitative data on students' sense of connectedness to each other, their advisory groups, and their advisors. Major findings revealed that enhanced advisory (EA) students' end-of-year mean scores on 12 of 16 positive development measures surpassed those of students in traditional advisory (TA), indicating that enhanced advisory played a role in fostering students' positive development. Qualitative data revealed that almost all interviewed students built a positive relationship with their advisors and benefitted academically, socially, and psychologically from that relationship. Many--but not all-- students also described the role of advisory in strengthening their connections to peers and sense of belonging to their advisory group.