This article describes an action research at an alternative high school which explores drop-out prevention strategies with first-year students. Student retention is extremely challenging for alternative schools. Because their mission is to provide a second chance to students who could not succeed in a regular setting, those schools regularly must deal with academically low-performing students, pregnant or parenting youths, or students with disciplinary problems. As numerous studies point out, these particular categories are at higher risks of dropping out of school. Bryant Adult Alternative High School in Alexandria, Virginia, has an average drop-out rate of about 60%. For a number of years, the school community has been striving to understand this problem and to find ways to fight it. In September 2007, the school faculty formed a drop-out prevention research group to gain a better insight into its drop-out rate, as well as to explore ways to reduce it. The research group decided to focus on new students because they constitute more than half of the student body at any given time. The school has an open enrollment that allows students to start the program at any time throughout the school year. Those students contribute significantly to the overall drop-out rate because one-third of them typically leave the school before the end of the school year. The research focused on three areas: (1) Collecting and analyzing statistical data of newly enrolled students, including their demographic information and academic history; (2) Analyzing new students' education values and commitment to earning a high school diploma; and (3) Mentoring as a means to promote students' success and reduce the number of students who drop out.