The purpose of the study was threefold: to understand security behaviours in practice by investigating factors that may cause an individual to comply with a request posed by a perpetrator; to investigate if adding information about the victim to an attack increases the probability of the attack being successful; and, finally, to investigate if there is a correlation between self-reported and observed behaviour. The study revealed that the degree of target information in an attack increased the likelihood that an organisational employee falls victim to an actual attack. Further, an individual’s trust and risk behaviour significantly affected the actual behaviour during the phishing experiment. Computer experience at work, helpfulness and gender (females tend to be less susceptible to a generic attack than men), had a significant correlation with behaviour reported by respondents in the scenario-based survey. No correlation between the results from the scenario-based survey and the experiments was found.