The aim of the study is to understand the role of insurance company reputation, performance, and positive/negative affect on health insurance policy customer retention and the moderating influence of customer inertia. A structured questionnaire was used for data collection. Covariance-based structural equation modeling was employed to assess the hypothesized relationships between the variables. The findings revealed that reputation, performance, and affect influenced customer retention in insurance sector. Positive affect had greater impact on customer retention in comparison to other constructs. Further, customer inertia was an important moderating influence on the negative affect for health insurance policy customer retention. To the best of our knowledge, the present study is the first of its kind that attempts to investigate customer inertia in the health insurance sector in an emerging market context, i.e., India. Customer inertia has not been much studied in light of company reputation, performance, and positive and negative affect in the health insurance milieu. The research findings may help health insurance companies understand the importance of reputation, performance, customer retention, and inertia while marketing insurance services.