Since its inception, the open source Assimilation project has been concerned with security, and paranoid at every opportunity. Like a lot of software, it has serious security concerns. On the one hand, our nanoprobes run on every server in the enterprise and exercise root privileges – creating a potentially dangerous attack surface. On the other hand, we incrementally create a high-value database which has fine-grained and up-to-date information about everything in the environment – software versions, ports, services, IP addresses and MAC addresses, known security vulnerabilities – a veritable treasure map for an attacker. This article details why cryptography is essential for communication in this environment, and some unique aspects of the problem we’re solving that affect how we use it. It is our hope our readers (this means you!) will give us a thorough flogging^H^H^H^H^H^H^H review of how we use cryptography in our software in this article and the next.