Abstract—A growing number of people use social networking sites to foster social relationships among each other. While the advantages of the provided services are obvious, drawbacks on a users’ privacy and arising implications are often neglected. In this paper we introduce a novel attack called automated social engineering which illustrates how social networking sites can be used for social engineering. Our approach takes classical social engineering one step further by automating tasks which formerly were very time-intensive. In order to evaluate our proposed attack cycle and our prototypical implementation (ASE bot), we conducted two experiments. Within the first experiment we examine the information gathering capabilities of our bot. The second evaluation of our prototype performs a Turing test. The promising results of the evaluation highlight the possibility to efficiently and effectively perform social engineering attacks by applying automated social engineering bots.