Purpose: To investigate the mediation effect of health insurance providers’ brand reputation (BR) on health insurance literacy (HIL) and intentions to purchase (IP) while assessing the moderated mediation effect of risk attitude towards health Insurance (RAHI). Methods: The study design is cross-sectional and quasi-experimental. The adapted questionnaire, which consisted of 20 items, was sent to respondents with the help of online surveys. A total of 229 complete respondents were analysed with the help of IBM SPSS V.23 and Andrew Hayes’ Process Macro 4.2, Model 7 for moderated mediation analysis. Results: RAHI, HIL, and BR are significant determinants of customers’ intentions to buy health insurance, affecting insurance providers’ marketing and communication strategies. RAHI is found to play a moderating role in health insurance literacy’s effect on insurance purchase intentions through brand reputation with a moderated mediation index of (B = −0.12, 95% CI = −0.21/−0.04). Conclusion: This study underscores the pivotal role of HIL in shaping the BR of private insurance providers and, consequently, influencing individuals’ IU private health insurance plans. Originality: This study's unique contributions are twofold to the body of knowledge; firstly, it highlights the BR’s mediating role on HIL and IP; secondly, it proves the moderated-mediation effect of RAHI on HIL’s influence on IP through BR. Practical Implications: Health Insurance providers shall take active measures to improve the HIL of potential customers with a focus on reducing the perceived risk. At the same time, measures should be taken to improve the brand reputation as it enhances the effect of HIL on IP.