Harnessing insights from Brophy's (1999, 2008, 2010) notion of scaffolding students' appreciation of learning, this article tackles challenges to student engagement, especially among reluctant students, by exploring two classroom settings in which students' valuing of school content and activities supported their engagement and achievement. The first model employed high-challenge tasks (extended writing tasks, collaboration, and multiday assignments) in eight 3rd-grade classrooms; the second highlighted connections made between student sense of identity and classroom activities among a diverse group of 9th-grade English students. Together, these models illustrate how practical strategies that support students' personal connection with, and therefore their appreciation of, what they are learning in school serve to empower self-sustaining engagement in learning.