Objective: The purpose of this study is to understand and explore the motivations and barriers faced by customers while purchasing Health Insurance. Design and Setting: An exploratory qualitative research design is applied to analyse the textual content of the depth interview data The theory of planned behaviour (TPB) provides the theoretical backdrop in designing the codes for the themes. Results: The major factors which motivated the respondents to purchase health insurance policy include financial security, cashless transaction, taxation benefits, continuity benefits and helping in medical emergency. The significant barriers in the purchase of health insurance as identified by the participants include factors such as all ailments not covered, all facilities not covered, affordability, lack of awareness, lack of clarity and regarding the expense as an unnecessary expenditure. Conclusion: The study uses the framework of TPB to ascertain the factors which contribute to the major themes during the course of content analysis. Our results indicate the factors which act as a motivation as well as the factors which act as barriers in the purchase of health insurance. A possible solution for such barriers is to widen the scope of financial literacy, to include the benefits of health insurance and make people aware of the details of such policies. Insurance companies should also try to reduce the premium charged.