In an era of increased accountability and diminishing financial resources, secondary schools across the nation are increasingly turning to online course offerings as a way to remediate and in some cases completely educate their students. In addition, students are opting to participate in online courses at an exponentially increasing rate for many reasons. Research within the cyber educational environment has primarily been focused on post-secondary students and institutions. There is a significant lack of understanding of how high school students function and achieve within the online environment. This dissertation used a mixed-methods approach, using both hierarchical linear analyses and student interviews to analyze student achievement data from an online provider and a central Indiana urban high school as well as gather student perceptions about their online experiences. The results of the investigation show that, in general, students performed better in their traditional school environment than in their online environment, and that there are specific demographic subgroups of students who especially struggled in the online environment. Specifically, students identified as "white" finished their online courses more frequently than their "black" student counterparts. Additionally, students labeled as "free lunch" students typically did much worse in their online courses than their "paid lunch" student counterparts. Further, the research uncovered a link between reading ability and a student's ultimate success in the online environment as well as a strong student preference for the traditional classroom due to the interactive nature of that environment. The implications of the findings for educational leaders are clear. They need to provide supports for online learners as well as direction for guidance counselors on how to select students for participation in the online environment. Additionally, the model for future online courses should be as the need much more attuned to the "read to learn" issue uncovered as well a for a more robust communication system between the learner and the online teacher. [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.]