Preschool special education students' lack of personal-social skills is affecting their kindergarten readiness and placing them at risk for exposure to school discipline in a large school district in the Southeastern United States. The purpose of this quantitative investigation was to examine the relationship between the quality of school discipline policies and personal-social skills of preschool special education students within the focus district. Data collection included archived personal-social skills scores, as measured by the Battelle Developmental Inventory-2 (BDI-2), of 354 preschool special education students. Four trained educators rated the effectiveness of the schools' discipline policies using the Teaching and Guidance Policy Essentials Checklist (TAGPEC). Preschool special education students' personal-social skills were measured using the BDI-2, and discipline policies were measured using the TAGPEC. Findings from simple linear regression analysis indicated no significant relationship between the TAGPEC ratings and students' BDI-2 scores. The personal-social skills for students in Title I and non-Title I schools (n = 96 students per group) were compared while controlling for TAGPEC ratings, but results showed no statistically significant differences. The average quality of the discipline policies was rated as inadequate overall. A policy recommendation was developed to encourage effective discipline policies and create a supportive school environment to promote positive social behaviors of all students, including the youngest and most vulnerable.