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Students with disabilities (SWD) experience disproportionately high dropout rates compared to their non-disabled peers, resulting in adverse academic, economic, and social outcomes. This study investigates the effectiveness of the Check & Connect Student Engagement Intervention, a structured mentoring program, in enhancing school connectedness for SWD. The research was guided by the overarching question: How does participation in Check & Connect influence micro-level factors of school connectedness among SWD with at least one alterable risk factor? Using a mixed-methods approach with a quasi-experimental pretest-posttest design and qualitative case study methodology, the study included 13 junior high school SWD in Central Massachusetts. Data were collected through surveys, academic and behavioral performance indicators, semi-structured student interviews, and an educator focus group. Quantitative results revealed statistically significant improvements in the experimental group's personal relationships with teachers, assignment completion, and cognitive engagement. While both the experimental and comparison groups experienced grade decline, the experimental group demonstrated a statistically significant lesser decline. Qualitative findings indicated that despite limited statistical significance in some indicators, the intervention meaningfully enhanced positive relationships with school personnel and improved academic, behavioral, and cognitive engagement. This study contributes to dropout prevention research by demonstrating that structured mentoring programs can enhance school connectedness to promote sustained school engagement among SWD. The findings highlight the need for equitable educational policies that prioritize school connectedness and system-wide implementation of evidence-based interventions to support at-risk student populations.