This qualitative comparative narrative study determined the perceptions of high school English language arts teachers regarding the impact of incorporating Web 2.0 tools upon student college readiness. This study also examined whether teachers should persist in incorporating Web 2.0 tools in educational experiences as they seek to support students in preparing for postsecondary educational pursuits. Using the conceptual frameworks of the SAMR and TPACK models, this study examined the impact of the integration of Web 2.0 tools for students in the classroom as well as how this integration prepares students for college readiness. This study also explored the incorporation of applicable professional development experiences for educators, specifically focusing on the implementation of digital tools in the classroom. Descriptive data was collected from three English language arts high school educators. Three cross-sectional interviews were analyzed to find the effectiveness of the use of Web 2.0 tools in English language arts classrooms on college readiness and the professional development opportunities of those educators. The study found that Web 2.0 tool integration benefits students' college readiness. Also, the results of this study revealed that technology-related professional development opportunities for educators affect student engagement and learning. According to this study, certain types of technology-related professional development opportunities for educators are currently not perceived as effective. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]