Affective engagement to school is a precondition for success among at-risk students who are learning in successful alternative high schools, which provide a second chance for schooling. Attachment is a well-known main characteristic of successful alternative schools. Yet while research indicated overwhelmingly positive psychosocial outcomes, academic outcomes of alternative schools yield mixed results. The current study investigated the narratives of the students who attend a successful alternative second-chance arts school. Our main purpose was to refine the main best practices for success as they reflect from students' narratives and to refine a theoretical model to illustrate these practices. The research consisted of 49 semistructured interviews with 36 students from all grade levels and internships of school. The results portray profound accounts of practices that enhance attachment to school and holistic pedagogical practices as two main essential practices, conceived by the interviewees that construct a genuine second chance when the two are intertwined. Enhancing attachment in a variety of methods and applying holistic pedagogical practices reduce school alienation and enhance success as they interact with one another. A theoretical model is presented to display the findings. Theoretical and practical implementations are discussed as essential for future policies regarding at risk youth for dropout.