There have been over 20 cryptoparties in New York City, in which people are introduced to open source cryptography software. This doesn't always go smoothly. Usability experts have only recently being included in the design process for encryption tools, but by and large what we have to work with were designed by cryptography experts in the 90s. I'll be going over some pain points between real-world users and their real-life encounters with open source cryptography tools.