Entering into this study years ago, I was bewildered at how disengaged so many high school students were in their education. They expressed their lack of connection with school by dropping out before graduating. Understanding that the real impact of education needs to happen between a teacher and a student, I became passionate about finding out what instructional strategies were being implemented at the secondary level that were engaging students in their learning. Schools are for the most part operating as a system of accountability instead of a system that engages students in learning (Schletchy, 2005). This research focused on interest-based instructional strategies that teachers in one high school used to engage their students in learning and how administrators supported their work. Using the method of portraiture by Lawrence-Lightfoot and Davis (1997), I identified three emergent themes of instructional strategies using interest-based techniques to promote student's engagement in learning: (a) Interest-based instructional criteria established by The Ohio Department of Education (2008) appeared to increase student engagement; (b) Administrative support, not direction, was necessary for teachers to develop, implement, and incorporate instructional strategies for student engagement; and (c) Time for teacher collaboration was a challenge but imperative in developing more wide-spread student engagement practices. Administrators and teachers in the study wholeheartedly felt interest-based instructional strategies was the way students should be taught in schools as we prepare them for their futures.