Abstract In recent years, governmental and industrial espionage becomes an increased problem for governments and corporations. Especially information about current technology development and research activities are interesting targets for espionage. Thus, we introduce a new and automated methodology that investigates the information leakage risk of projects in research and technology (R&T) processed by an organization concerning governmental or industrial espionage. Latent semantic indexing is applied together with machine based learning and prediction modeling. This identifies semantic textual patterns representing technologies and their corresponding application fields that are of high relevance for the organization’s strategy. These patterns are used to estimate organization’s costs of an information leakage for each project. Further, a web mining approach is processed to identify worldwide knowledge distribution within the relevant technologies and corresponding application fields. This information is used to estimate the probability that an information leakage occur. A risk assessment methodology calculates the information leakage risk for each project. In a case study, the information leakage risk of defense based R&T projects is investigated. This is because defense based R&T is of particularly interest by espionage agents. Overall, it can be shown that the proposed methodology is successful in calculation the espionage information leakage risk of projects. This supports an organization by processing espionage risk management.