Over the past two decades, early school leaving (ESL) rates in the European Union have significantly decreased, from 17.6% in 2000 to 9.5% in 2023. ESL refers to individuals aged 18–24 who leave education without upper secondary qualifications. Ireland has excelled by cutting its ESL rate to 4% in 2023 through initiatives like the Delivering Equality of Opportunity in Schools (DEIS) Plan and TUSLA Education Support Services. These programs address inequities by offering guidance, alternative pathways, and promoting attendance and retention. Despite progress, students from disadvantaged backgrounds, including migrants and Travelers, still face poorer educational outcomes. This research examines inclusive learning environments and their role in improving engagement, retention, and progression. Case studies from two high-performing designated DEIS schools illustrate how strong school leadership fosters effective interventions by building partnerships with families and communities. Applying Bronfenbrenner’s ecological systems theory, the study emphasizes the significance of interactions at the microsystem and mesosystem levels, supported by cohesive macro-level policies. The research identifies best practices for reducing inequities and improving outcomes across diverse educational contexts.