The ability to comprehend sophisticated text is a requisite skill for success at the collegiate level. Unfortunately, there is a large disparity between the complexity of texts used in high schools and those used at the collegiate level. Students may be underprepared if they have never been exposed to texts with the level of rigor that college demands. Underperforming college-bound students are those who have reading levels appropriate for their grade, but have reading levels below the demands of college-level texts. This trend is apparent in the vast numbers of students who fail to meet college-readiness benchmarks on the ACT exam but are proficient readers. The purpose of this proposed two-phase, sequential mixed methods study was to describe and understand why college-bound students who are underperforming in literacy fail to meet college readiness standards in comprehending college-level text in a large high school in the Rocky Mountain region. Findings from this study illustrate that students underperforming in literacy struggle with drawing appropriate inferences with sophisticated, expository text. Instead, they tend to over-rely on their own established set of comprehension strategies rather than employing strategies that would best suit the demands of the task at hand. Likewise, these students depend heavily on the instructional support of their teachers and are not able to function independently in the absence of the instructional support systems that are emblematic of testing conditions and the realities of the highly solitary expectations of the college experience. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]