This explanatory, mixed methods study investigated the relationship between students who currently attend Juniata College, as sophomores, and asked them to reflect on their high school technology experiences. All sophomores were invited to participate in a twenty-four question online survey, which included mostly quantitative Likert-style responses, with one open-ended text-based question. Out of the 400 students invited to participate, 140 completed the survey. The researcher used a series of pre-identified questions from the survey to identify those students who had the most and least technology experience base. A group of students were selected to represent the top and bottom 5% with strong or weak technology-based experiences. Through one-on-one interviews, these students expanded on their high school experiences and provided a rich context to the quantitative data they supplied from the survey. Six students were interviewed and provided the researcher with full details on the types of technology experiences they each encountered in high school and the impact they had on their perception of college readiness during their first year at Juniata College. Triangulation was used to provide a way to cross check results from multiple sources and identify regularities in the data. In order to obtain greater information regarding readiness, the researcher added a data component that provided insight into the relationship between the low-income status, assigned to each high school district, and college readiness. This helped the researcher better describe how the disparities between school districts' financial resources can impact the perception of college readiness. The findings of this explanatory, mixed methods study will provide high school and college teachers and administrators, particularly those involved with college freshmen, an understanding of how student preparation and exposure to technology impacts readiness for students' first year in college. The researcher will make recommendations on actionable items that can be followed to ensure students' success during their first year at a technology-rich post-secondary environment. [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.]