It is often an irony in organizational security: Although so much capital is invested in the protection of the organizational assets against external threats, some of the largest compromises have instead occurred as a result of insider threats, sometimes resulting in irrecoverable damage. This type of threat carries an especially high-risk factor for organizations in the sector of critical infrastructure and industries where intellectual property and the protection of sensitive information are essential for the healthy continuation of their operations.Employees in security-focused environments learn to treat outsiders with suspicion and to maintain trust boundaries. However, it is often the case that once an “outsider” enters the payroll of an organization they given a “carte blanche” in terms of trust and disclosure of information. They are now treated as the “insiders” that they are; members of the same tribe, fighting and working towards the same goals and using their skills to benefit their organization…until at some point one of them decides to use them differently. Or, until one of them realizes that the exploitation of organizational weaknesses would be a low-risk and high-reward activity. This talk aims to shed some light on the threat of insider activity. It will discuss the motives that lead employees to insider activity, such as the unauthorized disclosure of sensitive information, process corruption, electronic sabotage, and/or the facilitation of third-party access to organizational assets. Research has repeatedly found a clear link between insider activity taking place and exploitable weaknesses in an organization’s security and management processes. Therefore, this talk will go on discussing the organizational factors enabling insider threat operations as well as countermeasures against them, by combining the lessons learned on insider activity prevention from the fields of counterintelligence, psychology, and cyber-security.