Journal of Information Security Research Manel KHADRAOUI, Jamel-Eddine GHARBI 4 2 2013 http://www.dline.info/jisr/fulltext/v4n2/5.pdf Trust is a dynamic concept that evolves during a relationship. We study the initiation phase of trust toward an unknown website. We propose three sets of drives of initial trust: relational concepts (perceived value and satisfaction), in individual concept (trust propensity) and a contextual concept (structural assurance). We adopted the quasi- experimentation method for data collection. We have obtained 388 questionnaires. We have used structural equation modeling and we adopted multi-group analyses to test the moderator role of trust propensity.