Background: Even though oral disorders are among the most common diseases worldwide and have a considerable influence on private and public health expenditures, oral health is a neglected area of health. There is evidence that how dentists are paid can affect the type and amount of treatment they deliver. In Italy, oral healthcare is primarily paid for out-of-pocket, which carries the danger of under-servicing patients because of financial constraints. A limited public provision is managed through salaried dentists. The amount of care supported by employer-sponsored health insurance has significantly expanded because of recent legislative reforms. Methods: After a scoping review of quantitative and qualitative scientific literature on how the payment model could impact the provision of oral health care and a policy review on the intermediation of care through third-party payers in Italy, an interview guide was developed to interview seven Italian key-figures investigating their insight, perceptions, and acceptability on different payment mechanisms and how they impact on oral health care provision analysed through a thematic framework. Results: Public dentists recognized that the motivational role of being in a formative team compensated for the economic limitation attributable to salary, which doesn’t reward increased job efforts. Private dentists recognize how the reimbursement system affects clinical decisions made by both the dentist and the patient. They complained a severe reduction in reimbursement and an increase in administrative workload. They emphasized the complete absence of communication with the insurance companies, whose input they strongly value in order to deliver better care. Conclusions: Dentists support a legislative and policy intervention to promote dialogue with insurance providers and recognize the structure and management of insurance coverage as a powerful tool to influence the provision of care, both positively and negatively. According to dentists, these policy tools could improve both clinical outcomes, access, and quality.