Throughout the process of schooling from elementary through the end of high school; several points exist when students disengage from the process leading to dropout. The purpose of this phenomenological qualitative study was to identify the reasons for disengagement and dropout through the perceptions of the lived experiences of students. The qualitative study explored the lived experiences of 13 students who received intervention, disengaged, dropped out, and returned to obtain a diploma through alternative means. All involved students went on to higher or continuing education. Three themes (with sub-themes) and one over-arching theme emerged from the interview process that presented as reasons for disengagement and dropout. The three themes that emerged are connection to school, challenging or traumatic life event, and intervention timing, type, and benefit. The identified overarching theme that emerged is gender. The study analyzed the data via the modified van Kaam method. The study revealed common themes that educators can use to re-tool intervention in an effort to retain at-risk students. [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.]