This explanatory mixed-method study explored the dropout phenomenon from an ecological perspective identifying the school organizational (academics, activities, structure) and social relationship (teachers, peers) factors that most significantly influence students' decisions to leave school prior to graduation at a rural high school in south central Pennsylvania. The quantitative phase of the study utilized a 40 question, forced choice survey to isolate the school organizational and social relationship factors that had the most influence on students' dropout decision making, as well as to determine what, if any, correlation existed between the perceptions of students who are not at-risk, those who are at-risk but are still in school, and those who had already formally dropped out of school. The survey respondents included 80 students in school and 10 students who had dropped out of high school. The qualitative phase was composed of in-depth interviews of nine students who had formally dropped out of the rural high school in the study. The results of the quantitative analyses revealed the following key findings: (1) there was no single predictor factor category which statistically and significantly influenced student persistence; (2) there was no statistically significant difference in the way students who were at-risk, but still enrolled in high school, and those that had already dropped out perceived any predictor category; and finally, (3) the responses of students at-risk (whether enrolled or who dropped out) were statistically and significantly different from the responses of students who were not at-risk in the predictor categories of school structure and teacher relationships. The patterns that emerged from the interviews revealed that these students: (1) viewed the school structure as a barrier to diploma attainment; (2) believed the lack of content relevancy lead to detachment from school and justified the decision to quit school; and (3) shared that had an adult within the school intervened at the beginning of his or her divergence from the path to graduation, the results of his or her high school experience would have been different. Several implications for practice emerge given these findings. First, proactive strategies such as multiple curricular pathways and the use of transition academies should be applied systematically for all students enrolled in school. These structural elements of the school's organization should be paired with instructional strategies that promote student engagement. Second, targeted interventions should be designed to meet the needs of students who are at-risk for dropping out of high school. Targeted intervention should include the: (1) use of an instrument that identifies students who are developing or who possess negative perceptions of the school and school staff; (2) at-risk students being assigned an education advocate to promote meaningful and sustainable relationships; and (3) school leaders' efforts to creatively develop personalized learning for all students who are considered at-risk for early school departure. [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.]