In this paper, we show how trust develops (or fails to develop) during a simple interaction with a new website. We follow a group of students through a set of experimentally designed (between subjects) purchases to investigate where exactly trust is enhanced or hindered and by what. We adopt the conceptualization of Papadopoulou, Andreou, Kanellis, and Martakos (2001), which appears to capture the dynamism of the trust formation process. Our finding show that there are key points of “pressure” in the trust formation process that we need to investigate in more detail and that practitioners need to control in order to build and maintain online trust.