The purpose of this study was to measure teacher self-efficacy--that is, teachers' confidence in implementing one-to-one learning with Chromebooks and creating engaging lessons--to discover what training and/or materials, if any, are required to successfully implement a one-to-one Chromebook program at a middle school in Dutchess County, New York. This study was an analysis of practice that used a semistructured qualitative research approach consisting of convenience sampling to interview and observe teachers at a middle school in Dutchess County, New York, which implemented a new one-to-one Chromebook program 2 years prior to the commencement of the study. This study identified nine emergent themes involving the measurement of efficacy when implementing one-to-one learning with Chromebooks to create engaging lessons. Findings from this study identified areas of weakness in a one-to-one Chromebook program, and recommendations to the school district to help improve the program and support teachers are made. These findings could be used by other educational organizations looking to implement a one-to-one technology program in the future and provide a better understanding of the feelings, needs, and supports teachers will need when undertaking the launch of similar programs. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]