Tools that aim to combat phishing attacks must take into account how and why people fall for them in order to be effective. This study reports a pilot survey of 232 computer users to reveal predictors of falling for phishing emails, as well as trusting legitimate emails. Previous work suggests that people may be vulnerable to phishing schemes because their awareness of the risks is not linked to perceived vulnerability or to useful strategies in identifying phishing emails. In this survey, we explore what factors are associated with falling for phishing attacks in a roleplay exercise. Our data suggest that deeper understanding of the web environment, such as being able to correctly interpret URLs and understanding what a lock signifies, is associated with less vulnerability to phishing attacks. Perceived severity of the consequences does not predict behavior. These results suggest that educational efforts should aim to increase users’ intuitive understanding, rather than merely warning them about risks.