Automating software management is simple on almost every platform except Windows. Managing software deployments and upgrades typically entails manual, homegrown, or legacy approaches. We’ve seen more modern approaches to managing systems, sometimes called “DevOps”. Behind every great modern automation approach out there is a great package manager. Windows has long been left out of the conversation for DevOps due to a lacking solution for package management. Worse, with Windows, over 80% of the management and configuration deals with software installation management. However over the past 6 years, Chocolatey has become the de facto software management solution for Windows. Hundreds of organizations have turned to Chocolatey due to it’s extreme flexibility, common sense approaches, and building on well-known technologies like PowerShell. Chocolatey is a single, unified interface designed to easily work with all aspects of managing Windows software using a packaging framework that understands both versioning and dependency requirements. Chocolatey packages encapsulate everything required to manage a particular piece of software into one deployment artifact by wrapping installers, executables, zips, and scripts into a compiled package file. Chocolatey integrates with your favorite infrastructure management platforms, including Puppet, Chef, SCCM, and PowerShell DSC.