The goal of this evaluation was to provide findings and recommendations to the district on the one-to-one Chromebook program in connection to its stated goals around differentiation and 21st century learning within the context of a "high stakes" testing environment. This evaluation was conducted during year two of the one-to-one program, and the nine ninth grade teachers who served as the participants were involved with the program since its inception. Data were gathered over a three month period through small group and individual "naturalistic" interviews, classroom observations, document analysis, and an anonymous student survey that was administered via Google Forms. The evaluation produced findings in the following seven areas: vision and mission, implementation, defining differentiation, differentiating teaching and learning, high stakes testing, 21st century skills, and further education. The overall findings suggested that while the one-to-one Chromebook program helped the high school (and district) to further realize its desired goals around differentiation and 21st century learning, both the degree and ways in which Chromebooks were used across the disciplines were inconsistent. Each of the teachers involved in this evaluation was positive about the one-to-one program, they indicated that it was a success, and they identified specific areas for future professional development that was specific to their respective discipline. Finally, specific recommendations were provided to both the local Board of Education as well as the state/federal legislature based on the data gathered. The recommendations focused specifically on what was needed for schools to further allow technology to enhance teaching and learning while helping students to develop 21st century skills. [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.]