Oral health complications are the most common adolescent chronic illness and reason for school absence. Because of financial and structural reasons, oral healthcare remains inaccessible to many. A few attempts have been made to deliver dental care to children at school. Still, little is known about the experiences of various providers—dental hygienists, dentists, care coordinators—in these settings. In this paper, I explore the opinions and suggestions of care providers who have worked in schools to provide an analysis of such programs from the perspectives of several stakeholders. Using semi-structured interviews and qualitative analysis, I find that in-school dental delivery faces several obstacles to successful operation, along with several effective measures currently in place, and detail what care actually looks like in school-based programs and how disconnects between public health and non-public health dental workers impact care. Based on these findings, I argue that the current system needs to be enhanced by funding and policy that liberates dental hygienists, subsidizes dental procedures, and allows for the use of tools that mobilize care. This insight may help guide future ADA or state dental policy, with the potential to expand access for all.