Developing online trust is crucial for e-commerce vendors in order to attract consumers and develop long-term relationships with existing ones. We intended to investigate if consumers from different generational cohorts differ on how they develop online trust when utilizing e-commerce websites. Through the analysis of empirical data collected from 138 users of e-commerce, we examined four drivers of online trust between three generational cohorts in Puerto Rico. We reviewed relevant research related to the effects of security, privacy, navigational elements, feedback mechanisms on online trust and generational cohort theory. Partial least square and structural equation modeling was use for analysis. Results suggest that online trust is developed in dissimilar fashions across generations and differ in what drivers they find important. Our research could hold practical and scholarly significance since its findings can help ecommerce and online service providers in determining the important factors they need to have present in their websites in order to address online trust for their target audience. By investigating the differences in the drivers of online trust across three generational cohorts, this study builds upon previous literature that only compared Millennials against Baby Boomers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]