The present paper represents work in progress, the goal of which is to further our understanding of the process through which people come to trust an e-commerce web site enough to engage in a transaction. Following a brief literature review, the authors will examine the role of personcentered mediating factors in the decision to trust or not to trust an e-commerce site. Specific constructs, such as self-efficacy, levels of both computer and Internet knowledge and experience, and trust and distrust will be investigated, leading to the formulation of a research model for the development of tendencies to trust or distrust, and the relationship of these tendencies to high and low risk transaction-relevant behaviors. Preliminary statistical analyses reveal some support for the model. Higher risk online behaviors such as a tendency to make purchases or pay bills online was better predicted by lower levels of Distrust, while Trust was a better predictor for lower risk behaviors such as searching for product-related formation, or news and sports information.