To address the needs of middle school students who experience difficulty with reading, students are often placed in reading intervention programs to improve literacy skills. This study explores the question: in what ways do students successfully and unsuccessfully use self-initiated comprehension strategies in their efforts to engage with challenging texts? A case study of four seventh-grade students gives insight to how students engage with difficult texts through self-selected strategies. Placing an emphasis on students' strengths, building positive student relationships, and valuing students' abilities can encourage adolescents to transcend beyond deficit labels.