This research explored what students and school staff in rural, low socioeconomic (SES) high schools perceive as factors that strengthen and inhibit the positive youth development (PYD) attributes of students' confidence, competence, character, connection, and compassion. A collective case study was conducted in four rural high schools, two in Kansas and two in West Virginia. Fieldwork at each school involved semi-structured focus group interviews with students and school staff. Observations and documents collected focused on the various social-emotional learning (SEL) support, services, and opportunities made available to students as well as community resources and statistics. It was discovered that students and school staff perceive that a student's lack of understanding and acceptance of others, a challenging and disruptive home life, and the pressure to perform academically can be significant inhibitors of all five PYD attributes in rural, low-SES high schools. Providing diverse opportunities for student engagement and hands-on and engaging courses, such as Career Technical Education (CTE) combined with adult intentionality, modeling, and encouragement, emerged from the study as perceived factors that strengthen all five attributes of PYD. The recommendations section of this paper provides thoughts and suggestions on strengthening the PYD of students attending rural, low-SES high schools.