Systems and methods are disclosed for determining whether a third party observer could determine that an organization has an intent with respect to subject matter based on the organization's web activity. The determination that there is a risk of information leaks to the third party observer can be completed by analyzing the entropy of web usage information destined for the third party observer's servers. Systems and methods are also disclosed for mitigating the risk of information leaks by obscuring the organization's web activity. The web activity can be obscured by selecting candidate actions that can be used to generate neutralizing web traffic from the organization's network which will obscure an intent with respect to a particular subject matter. For example, the candidate actions can identify specific queries, links, or actions that the organization can take to neutralize their web activity to a less remarkable point in the search space.