This paper brings together the experiences of children, teachers, and parents in two very different schools in Jamaica—one primary and one preparatory. The data are taken from two larger qualitative studies. The first, An Exploration of Two Classrooms: Cases in Classroom Management, is a case study of a grade 5 teacher’s classroom management strategies in a government primary school and her interaction with four of her students—selected because they were highly responsive and promised to be information-rich respondents. The second study, The Good Morning Bird, The Good Night Bird: Children Painting Their Experiences of Success in the Educational Landscape, is a phenomenology of three children in a grade 1 class in a private preparatory school. The children are the chief participants in this study, with their teachers and parents as “expert guides''to their home and school worlds. Maximum variation sampling was used to select the participants in the phenomenology, thus allowing children of very different academic abilities to be included.