This mixed method survey study examined the inter-relationships between teaching styles and the depth of classroom-based technology applications used by teachers participating in 1:1 digitally enhanced classrooms in thirteen of Alaska's rural school districts. The promise of technology to catalyze the transformation of schools into learner centric environments preparing students to be 21st century learners has not been realized. Significant first order barriers have limited the digital learning resources necessary to systemically affect pedagogical change. During the last six years, various entities have sponsored digitally enhanced learning environments to stimulate the process of education reform. These initiatives, labeled as one-to-one (1:1), brought teachers face-to-face with the challenges related to second order education reform while creating an opportunity to study changes in instructional philosophy and practice as a result of teaching in an environment rich in technology. This study explored three questions formulated to probe the relationship between pedagogical philosophy and the application of 1:1 technology to support learning: (1) "What is the relationship between instructional philosophy and the way teachers use technology to support learning in Alaskan high school 1:1 laptop programs?"; (2) "How does access to a 1:1 classroom affect a teacher's instructional philosophy or practice?"; and (3) "Does access to a 1:1 digitally enhanced teaching environment facilitate the use of instructional practices consistent with Alaska Native and 21st century learner outcomes?." Ninety-four rural high school teachers responded to a survey that assessed teaching styles on a continuum from transmission to constructivist. The level of technology adoption was examined using three indices that respectively measure the professional, personal and classroom use of technology by teachers. Information derived from open ended questions was triangulated with quantitative data to develop a meaningful understanding of the study questions. Quantitative and qualitative data suggested that the majority of responding teachers identified with constructivist beliefs over traditional transmission. Teachers noted a strong positive relationship between teaching and the application of technology, yet analysis showed that constructivist beliefs were attenuated by several challenges related to management of technology. While teachers were generally aware of the potential for digital learning technologies to support Alaska Native and 21st century methods, they were outweighed by operational concerns related to the integration of technology. These study questions are significant. Digitally enhanced instructional practices help to equip students with the skills expected of 21st century learners. Perhaps even more significant is the congruence between the teaching styles traditionally used by Alaska Natives and the digitally enhanced constructivist practices made possible when using technology to augment processes for acquiring knowledge. [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.]