A qualitative case study was completed over approximately a five week period from April 20 to May 25, 2007. The goal of the study was to discover what attitudes, perceptions, and literacy benefits three different middle school reading tutors had in response to tutoring struggling beginning readers. The study also was interested in what the three students reported about self regulating reading strategies used during the tutoring experience. The data collection consisted of methods such as observations, field notes, surveys, interviews, and reading comprehension analysis. The data was then complied and analyzed to create individual cases of each participant, which were then cross-analyzed with each other and compared to established theoretical foundations. The findings and results were consistent with the researcher’s stance that cross-age tutoring experiences and metacognitive strategy use are intertwined in improving a reader’s self-efficacy, which can improve the overall reading literacy of individuals.