This dissertation, organized in chapter format, is comprised of a collection of case studies designed to explain why some teachers are not prepared to meet the challenges of the National Education Technology Plan despite the pervasive evidence of technology in our personal and professional lives. The first case study is the personal history of one teacher who "battles the machine" and is reluctant to alter what works in her current practice. The next chapter is a multiple case study that examines the issues and challenges experienced teachers faced in their efforts to become more fluent in the use of educational technology. Using an extensive technology related professional development event as an intervention, the study explores teachers' use of technology before and after the inservice, the role of professional development in building technology skills, and matters related to the sustainability of skills. Teachers stressed the need for ongoing support in the form of a knowledge broker to assure continued efficacy and proficiency while integrating technology into their content and their practice. The fourth chapter, after a five year lapse, revisits two teachers from the previous multiple case study and introduces a new tech savvy teacher who shares her experiences as a new integrator of technology. Self report is used to examine the issues and challenges these experienced teachers faced in their efforts to become more fluent in the use of educational technology. The teachers in this multiple case study participated in a number of technology related professional development interventions over a period of approximately four years. This chapter includes their reflections on the successes and failures as they continue to grapple with the challenges of increasing their technological, pedagogical, and content knowledge or TPACK and create change in their practice. Included is an essay presenting a proposal for a framework of five phases of professional development to support the federal government policies of No Child Left Behind and the National Education Technology Plan. The framework is upheld by five principles of professional development considered crucial for effectively changing teacher practice to incorporate instructional technology into the curriculum. By superimposing these principles: duration, content, active learning, and collaboration, this essay then positions technology related professional development as ongoing with the support of professional learning communities or networks and knowledge brokers as a means of sustaining and expanding the efforts teachers make toward technology fluency. The concluding chapter discusses how education systems constrain teachers' effort or ability to changes. Recommendations are provided on how relations among teachers and institutions might be reconfigured to promote more and better professional learning and practice in technology. [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.]