Modern encryption techniques provide several important security properties, well known to most practitioners. Or are they? What are in fact the guarantees of, say, HTTPS TLS cipher suites using authenticated encryption, IPSec vs. SSL VPNs, Property Preserving Encryption, or token vaults? We live in an era of embedded Hardware Security Modules that cost less than $1 in volume, and countless options now exist for encrypting streaming network data, files, volumes, and even entire databases. Let's take a deep dive into the edge of developed practice to discuss real-world threat scenarios to public cloud and IoT data, and look closely at how we can address specific technical risks with our current encryption toolkits. Advanced math not required.