This paper reports the highlights of a user study which gauges reactions to a variety of common “trust indicators” – such as logos, third party endorsements, and padlock icons – over a selection of authentic and phishing stimuli. In the course of the think-aloud protocol, participants revealed different sensitivities to email messages and web pages. Our principal result is the analysis of what makes phishing emails and web pages appear authentic. This is not only of interest from a pure scientific point of view, but can also guide the design of legitimate material to avoid unnecessary risks. A second result of ours are observations of what makes legitimate content appear dubious to consumers. This is a result with obvious applications to online advertising.