This article draws on a phenomenological study of understanding six early adopters’ successful online shopping experiences. Narratives of their online purchasing experiences suggest that learning to trust e-tailers is a complex process that is shaped by factors such as self-identity, risk awareness, and technical and brand knowledge. This article summarises the first part of the findings from this study – the strategies the six participants used to gain trust with e-tailers to overcome their distrust of purchasing online. These strategies included checking payment security, gaining product information, checking the ordering process, using brand knowledge, asking friends for advice, using expert referrals, and assessing website structure, functionality and image. The findings suggest that technical and/or brand knowledge best explain the methods that these participants used to trust e-tailers because it provided them with a greater sense of comfort to purchase online. As with offline marketing contexts, this research suggests that credibility and benevolence are two important underlying dimensions of online trust. However, due to the distrustful environment of e-commerce, honesty may be an important separate dimension of online trust.