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Organisations today operate in a world fraught with threats, including “script kiddies”, hackers, hacktivists and advanced persistent threats. Although these threats can be harmful to an enterprise, a potentially more devastating and anecdotally more likely threat is that of the malicious insider. These trusted individuals have access to valuable company systems and data, and are well placed to undermine security measures and to attack their employers. In this paper, we engage in a critical reflection on the insider threat in order to better understand the nature of attacks, associated human factors, perceptions of threats, and detection approaches. We differentiate our work from other contributions by moving away from a purely academic perspective, and instead focus on distilling industrial reports (i.e., those that capture practitioners’ experiences and feedback) and case studies in order to truly appreciate how insider attacks occur in practice and how viable preventative solutions may be developed.