Preparing students for 21st-century learning is a great responsibility and a challenge for many school districts across the country. A large body of research suggests that a school district's level of awareness with regards to education technology and particularly those technologies that are on a positive trend correlates with a successful technology implementation program. District Administrators that lead the charge of developing technology policies and oversee the various aspect of the technology implementation must possess a solid awareness of modern education technologies and their interplays with curriculum and pedagogy. In addition, district Administrators must have the technological skill to overcome network infrastructure capabilities constraints as well as the leadership skill to prioritize technology. This study used a survey as its main method of data collection; the survey was guided by three research questions that helped gain valuable insight about California K12 school district Administrators' familiarity with most relevant modern technologies and strategies for educating students in the 21st-century, knowledge of intermediation between (technology, pedagogy, curriculum), as well as what Administrators perceive as constraints that impede effective technology implementation. The data shows that majority of district Administrators reported to having insufficient knowledge of modern and emerging technologies or digital strategies that are most reliant on technology, in addition, the data suggest that district Administrators are finding funding, training, and infrastructure as main factors that impede implementation of technology appropriate for a 21st-century education. The results of this study propose recommendations that have implications for K12 school districts' technology awareness, knowledge acquisition for technology preparedness, district technology plan, and minimum technology readiness requirement for school district Administrator positions for the 21st-century. [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.]