The Smallville Independent School District case study highlights the challenges of a school district facing the COVID-19 pandemic in a rural–urban divide. The district’s socioeconomic status, with a high population of economically disadvantaged families, limited resources, and dependence on grants and local charity, further complicates matters. The district’s new superintendent was hired, expecting her experience to help address the district’s challenges. Teacher retention and technology integration were critical areas of focus. However, resistance from some board members added to the already-existing racial tensions in the town, making it a challenging environment to implement change during a pandemic.