This qualitative case study explores the influence of outdoor learning on high school student's engagement in core academic content courses. Students placed at risk of school failure benefit from instructional supports that help them stay engaged in learning. This study examined the learning experiences of 14 at-risk students within four grade 9 and 10 core classes, including English 1-2, Biology 1-2, Algebra Explorations 1-2, and Geometry 1-2. Each student participant was observed across three separate outdoor lessons. Students took photographs of their experiences in the outdoors and participated in photo-mediated individual and/or focus group interviews. Three teacher research participants provided lesson plans for review and participated in interviews before and after class observations. Study findings support a growing body of research that connects high quality learning environments with student engagement: academic, behavioral, psychological, and social. Teacher assessments, student reports, and student class grades reflected increased conceptual understanding of core concepts through hands-on learning activities supported by group work in a number of flexible, open spaces on campus. The students appreciated the fresh air, green environment, open spaces, views, ease of movement, and close relationship to nature. They also valued having a choice of how and with whom they worked, as well as freedom from the direct supervision of their teachers. Students also voiced appreciation for their teachers' demonstrated respect and trust in them. Study findings advance understanding how teachers leverage certain facility and school site conditions and design features to increase student engagement in learning. These findings inform school and district leaders' decisions regarding educational facility planning, design, and use.