Alternative high schools serve some of the most vulnerable students and their programs present a significant challenge to evaluate. Determining the impact of an alternative high school that serves mostly at-risk students presented a significant research problem. Few studies exist that dig deeper into the characteristics and strategies of successful alternative schooling. Moreover valid program evaluation methods to identify successful alternative school practices are hit and miss. As a result, public policy and systems of accountability have either disregarded information relating to alternative high schools or unjustifiably included them in comparisons with traditional high schools. This dissertation studied the issue of how best to evaluate alternative high schools and what tools support leaders in planning a thorough and accurate program evaluation. The "Alternative High School Program Evaluation Toolkit" was developed to support school leaders and evaluation teams made up of internal and external stakeholders as they facilitate the program evaluation process. The features of the Toolkit address the need for alternative school evaluation to be practical, useful, fair and accurate. The Evaluation Toolkit includes training materials, protocols, an evaluation planning worksheet and an evaluation planning matrix that supports the team in conducting the evaluation. The research represented in this dissertation is theoretically and practically grounded in Bridges and Hallinger's (1995) Problem-Based Learning (PBL) and Borg and Gall's (1989) Research and Development (R&D) Cycle. The product of the R&D Cycle was the "Alternative High School Program Evaluation Toolkit" and a process for use by evaluation teams assigned the task of planning and carrying out program evaluations. [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.]