Factors influencing teachers' levels of technology self-efficacy were examined through a qualitative multi-site, multi-subject case study research design. An initial survey was administered to all full-time, certified teachers at three school sites in order to gauge teachers' current level of technology self-efficacy. From that population, purposive and systematic samplings were used to draw the participants for the case study. A group of nine teachers with varying levels of technology self-efficacy was interviewed and participated in one of three focus groups to better understand factors influencing their current level of self-efficacy. A document analysis was also performed of local school professional development plans. Results revealed several factors that influenced teachers' technology self-efficacy, including personal, behavioral, and environmental factors. Common themes emerged that indicate more can be done to foster increased technology self-efficacy in teachers, which may in turn enhance students' learning experiences. [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.]