|The indicators and predictors of dropout as documented in the literature are vast and encompass influences such as family, motivation, socio-economic status, and academic achievement, and could be accepted as universal reasons students choose to leave school and not return. This qualitative study investigated the reasons why students in one West Virginia county choose to drop out of school. Using cross-case analysis, the perceptions of current students identified as at-risk of dropping out, former students, and Attendance Directors and Guidance Counselors were explored to determine emergent themes and provide proactive and reactive strategies to prevent dropout. This study resulted in two major themes emerging from the data collected, and it was determined that all participants perceived Attitude about School (i.e., teacher attitude, academic attitude, and family attitude) and Drama (i.e., fighting and peer acceptance), as having significant impact on a student? decision to drop out. Through an application of ecological systems theory as a theoretical framework for the study, each case study provides representation of the micro- and macrosystems that directly influence the student? reciprocal transactions within the mesosystem of the school and in the microsystem of self. If dysfunctional, these transactions between student and environment can propel a student on the path to dropping out. The results of this study provide recommendations for change that can assist West Virginia Schools in preventing dropout such as professional development for teachers, peer mentoring, in-school support groups, and more traditional roles for school social workers and guidance counselors.