This article reports the findings of a study that examined how middle school struggling readers transact with the reading task demands of his or her respective classroom. The study also examined how each student's teacher transact with the student's reading challenges. The author used a descriptive, case study approach. Findings showed that the ways in which each student transacted with the reading task demands of his or her classroom were influenced by: (1) his or her perception of his or her abilities as a reader, (2) how he or she wanted to be seen as a reader, and (3) his or her desire to comprehend and learn from text. On the other hand, the ways in which each teacher transacted with his or her respective student in relation to the reading task demands were influenced by (1) the teacher's perception of the student's cognitive strengths and weaknesses as a reader and (2) how motivated the teacher thought the student was in trying to apply behaviors that might increase comprehension.