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Introduction: Multiple job holding (MJH), the phenomenon of working in more than one paid job simultaneously, affects the achievement of universal health coverage. The dearth of research on MJH among dentists, especially in Africa, forms the backdrop to this study. This study aimed to explore the perspectives of key policy actors on MJH among dentists in Nairobi, Kenya. Methods: This qualitative study combined semi-structured interviews with key informants and in-depth interviews with dentists who are engaged in MJH. The key informants were selected purposively from the Kenyan government, the regulator, representative organizations of dentists, and oral health researchers and/or experts in human resources for health. The dentists were selected from the government, the private sector, and faith-based organizations, using snowball sampling. The interviews focused on knowledge and/or experiences of MJH, reasons for, and the consequences of MJH. The interviews were analyzed using thematic analysis. Results: Thirty interviews were conducted, comprising 20 key informants, and 10 dentists. MJH among dentists is seen as a normative practice, facilitated by a profession characterized by high rewards and few or no adverse consequences from absenteeism. Although additional income is the primary motivation for MJH, low job satisfaction, the lack of continuing professional development, perverse incentives, and a dysfunctional and resource-constrained public health sector exacerbate MJH. The lack of regulation compounds the practice, while a strong private health sector provides opportunities for multiple sources of income, affecting the provision of oral health services negatively in the public sector. Conclusion: MJH among dentists in Nairobi, Kenya is common because of high rewards and few or no adverse consequences from absenteeism. The high reported occurrence of MJH requires a multi-pronged approach that combines individual, system, and structural interventions. Such an approach should also consider the drivers of MJH, and ensure collaboration among policymakers, dentists, and health service managers to develop strategies to mitigate the potential negative consequences of MJH for patients, the health workforce, and oral healthcare delivery in Nairobi.