E-commerce can enhance its acceptance among users through fostering online trust, which is vital for decision-making process. The perception and computation of trust is crucial for vendors and users for the success of e-commerce. The calculation and measurement of trust antecedent involves complex aspect such as presence of security controls and familiarity within the website. Most companies are acquiring ‘security technology’ because everybody else is doing the same, but not because there has been a proper assessment of its association with trust. The purpose of this paper is to analyze the role of trust antecedents such as security, and familiarity when they are used collectively to do online transactions. Trust, in general, is an important factor in conducting e-transaction, which revolve around uncertainty and ambiguity. The Fuzzy logic approach provides a means for coping with this uncertainty and vagueness that are present in e-commerce. Therefore, the fuzzy logic approach is been deployed to develop scales to measure the effects of users’ familiarity and perception of security in an online business-to-consumer (B2C) context. This research provides guidelines to vendors on how they could ascertain the trust level of their business and ways of mitigate the negative impact on the trust level.