PurposeResearch on online businesses has focused on the adoption of e-commerce and initial purchase behavior; repurchase intention and its antecedents remain underresearched. The present study develops an empirical model to explore the extent to which trust and e-satisfaction mediate the effect of vendor-specific attributes and customer intention to repurchase from the same online platform.Design/methodology/approachThe proposed model is tested and validated in the context of Generation Y in India. A self-administrated online survey was employed, and the students aged between 20 and 35 at universities in Northern India are selected as subject. The data is analyzed using SPSS 20.0 and AMOS 20.0, where structural equation modeling is used to examine the model and test the hypothesis.FindingsThe results of this study suggest that trust mediates fully between security concerns, privacy concerns, and repurchase intention. E-satisfaction mediates between security and ease of use (EOU).Practical implicationsThis study reveals the fact that security, EOU, and privacy concerns are the critical determinants that have the most impact on consumer's purchasing behavior. Gen Y consumers of India need some strong security features, an easy-to-use interface, a trusted privacy policy. Furthermore, it may be beneficial to observe e-satisfaction and trust as a mediator when identifying potential problems; online satisfaction is essential for the group in this study, and the results show that it impacts on the relation between repurchase intention and some determinant of repurchase intentions.Originality/valueThis research determines the impact of security, privacy concerns, EOU on the online repurchasing behavior of Gen Y in India. The mediation effect of e-satisfaction and trust has also been determined.