School nurses are pivotal to the safety of school-aged children, particularly those who receive medications in the school setting. The purpose of this study was to explore factors associated with medication administration errors in North Carolina school districts between 2012/2013 and 2017/2018. A longitudinal study using repeated measures analysis of school health services data collected in the North Carolina Annual School Health Services and Programs Survey was conducted. Over time, the number of medication errors (p = 0.001) and number of medication corrective action plans (p < 0.0001) trended upwards. There was also an increase in medication errors when the number of schools in a district was higher (p < 0.0001). Conversely, there was a decrease in corrective action plans when school nurses were directly employed by the school district (p = 0.0471). We implore school districts to consider the important role of school nurses to keep kids safe, healthy, and ready to learn.