The number of students choosing to drop out of school before earning their high school diploma continues to rise at alarming numbers. These students cause educators to question what strategies can assist struggling learners with academic, behavioral, or health issues to increase their chances of completing high school. Many dropout prevention programs help provide innovative methods and practical strategies to increase the number of at-risk students remaining in school instead of dropping out. These programs provide at-risk students with a variety of academic structures, social, and emotional support services to meet their interests and needs. This study looked at work-related dropout prevention programs for high school students at alternative schools in urban schools in New York State. These alternative schools have implemented dropout prevention programs to address at-risk students who are likely to drop out due to circumstances at their traditional school. Students identified for these programs are usually behind in credits and are seen as at-risk of not graduating in four years after the first year of high school. Additionally, these students are behind in a grade level, under-credited, have high absenteeism, and have not been unsuccessful in a traditional school setting. More importantly, staff members working closely with these students have worked in these dropout prevention programs and have continuously monitored at-risk students on a weekly/monthly basis. This study identified school administrators' perceptions of the effectiveness of work-related dropout prevention programs and how they support at-risk students. The results from this study suggest that school administrators perceive the most effective dropout prevention strategies to motivate students are captured through engagement and collaborative learning. [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.]