Discover how to automate your Windows development environment setup using Chocolatey and Boxstarter in this comprehensive 52-minute conference talk by David Gardiner, an experienced package author and Chocolatey.org moderator. Learn to script your desktop, creating a fully configured developer environment from a vanilla Windows install in minutes. Explore the process of wrapping tools and applications in Chocolatey packages, avoiding common pitfalls, and gaining insights into the package moderation process for confident publishing to Chocolatey.org. Master the orchestration of package installations, including handling reboots, with Boxstarter. Understand how these techniques can be applied not only to rebuilding dev boxes but also to simplifying software distribution and upgrades for customers. Suitable for Windows-based developers of all levels, this talk aims to increase coding time by streamlining software installation and configuration processes.