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.