Cryptography has become ubiquitous in communication technology and is considered a necessary part of information security. However, both the regulation to restrict access to cryptography, as well as practices to weaken or break encryption, are part of the States’ security policies. The United States (U.S.) regulate cryptography for export in international trade as a dual-use good. However, the regulation has been increasingly loosened and transferred to bilateral agreements with Information and Communication Technology companies. At the same time, the National Security Agency attempted to implement a government encryption standard to guarantee itself easier access to data, thus progressively expanding surveillance on non-U.S. citizens. In this paper, using comparative policy analysis, we examine the evolution of both security policies by tracing the historical development of U.S. regulation of cryptography as a dual-use good, and surveillance technologies, and practices used from the 1990s to today. We conclude that the impact of the dual-use regulation has affected the efficiency of surveillance technology, by loosening regulations only for mass communication services, thereby supporting the proliferation of surveillance intermediaries, while working on strategies to collaborate and exploit their coverage.