This research evaluates inpatient care educational programs for children with special health care needs, and both hospitals’ and schools’ capacity to effectively support these students as they transition back into “typical” school settings. This research assesses the current inpatient and outpatient systems’ effectiveness in supporting children during their transition. In ineffective cases, the research seeks to understand methods that could improve such programs. Twenty, semi-structured interviews with healthcare professionals, school nurses, teachers, social workers, and therapists were conducted to evaluate the effectiveness. The research highlights the negative impact of low school attendance on medically fragile children. It was found that a common home-hospital liaison or the use of a centralized database could create fluent and effective communication between all parties. Without a cohesive device for communication, the transition for students with healthcare needs becomes fraught and risks significant negative impacts on the child’s educational progress. The research provides an opportunity to create positive change in the disability, education, and healthcare communities by emphasizing the individuals’ voices who are impacted by these disparate systems.