Adolescents' perceived connection to school has been consistently associated with positive development across a range of domains, with strongest evidence for the quality of student-adult relationships in school as a core factor. Using a purposive sample of 32 high school seniors from 9 urban schools who had participated in a quantitative study 5 years prior, this multimethod study examines the experiences that promote or undermine these adolescents' feelings of connection to school--in particular, their feelings of respect for and caring by teachers, and their sense of belonging to their schools. Adolescents in our sample respected teachers with engaging instructional styles and a commitment to student learning; most viewed even small efforts by teachers to get to know them as evidence of caring. Further in-depth analysis of 5 participant cases using interview data and quantitative data from middle and high school provides a contextualized view of adolescents' trajectories of connection to school over time, and highlights the differentiated profiles of belonging to school and affective relationships with teachers reported by these youth. Theoretical and methodological implications for the study and promotion of perceived school connection are discussed.