Insider threats are a growing concern to both public and private entities. Like other threats within the cyber realm, these threats tend to be dynamic in nature. Organizational structures and varying motivating factors of threat actors can impact the effectiveness of mitigating technologies and strategies. This paper explores the gaps that result when organizations try to segment logical and physical assets, which in turn creates the opportunity for collusion or coordinated attacks. In this paper, various data sources have been examined to identify organizational patterns that can potentially contribute to the successful outcome of these types of attacks. A motivating example is then presented, in junction with the data, to hypothesis what percentage of organizations would be able to identify the actions of insiders working in tandem based on the current state of the industry.Index Terms-Collusion attack, coordinated attack, cyber threats, insider threat.