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Chocolatey Training — Windows Package Management & Software Automation for DevOps

Master Chocolatey: package installation, creation, internal repositories, and CI/CD integration. Windows package management for DevOps, system administration, and infrastructure automation.

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What Is Chocolatey?

Chocolatey is the package manager for Windows — bringing APT/YUM-style package management to the Windows ecosystem. With choco install, system administrators and DevOps engineers can automate software installation, upgrade, and removal across Windows server fleets and developer workstations. Chocolatey packages wrap traditional installers (MSI, EXE) with automation logic, enabling consistent, scriptable, idempotent software management on Windows.

Role in DevOps

Chocolatey bridges the package management gap between Linux and Windows in DevOps. Ansible's win_chocolatey module, Packer Windows builders, and CI/CD agents all use Chocolatey for automated software provisioning. Internal Chocolatey repositories (hosted in Nexus/Artifactory) provide governed, auditable software distribution — equivalent to a private APT/YUM repository for Windows. For organizations managing hybrid Linux/Windows infrastructure, Chocolatey is an essential tool.

Who Should Attend

  • DevOps engineers automating Windows infrastructure
  • Windows system administrators managing software across server fleets
  • Build/release engineers creating internal Chocolatey packages

Learning Outcomes

  • Install, upgrade, and manage software with Chocolatey commands
  • Create Chocolatey packages for internal software distribution
  • Host internal Chocolatey repositories in Nexus or Artifactory
  • Automate Chocolatey with Ansible for Windows infrastructure
  • Integrate Chocolatey into Packer for golden Windows images

Course Modules

  1. Chocolatey Fundamentals — Architecture. Commands (install, upgrade, uninstall, list, search). Package sources.
  2. Package Creation — nuspec files. chocolateyInstall.ps1. Package testing. Publishing to community feed.
  3. Internal Repositories — Hosting in Nexus/Artifactory. Package approval workflow. Version management.
  4. Chocolatey in Automation — Ansible win_chocolatey. Packer provisioning. CI/CD agent setup.
  5. Enterprise Chocolatey — Licensed features (C4B). Package internalizer. Central management. RBAC.
  6. Capstone: Windows Package Automation — Build an internal Chocolatey repo, create packages, automate with Ansible.

Hands-on Labs (8 total)

Install and manage software with Chocolatey. Create a Chocolatey package for an internal tool. Set up a Nexus-hosted Chocolatey repository. Automate Windows software installation with Ansible and Chocolatey. Build a Packer Windows image with Chocolatey-provisioned software.

Related Courses

See NuGet Training for .NET package management, SysOps Training, and Ansible Training.

TOOLS_COVERED

Chocolatey PowerShell Ansible Packer Nexus Artifactory

PREREQUISITES

  • Windows administration basics
  • PowerShell fundamentals

CURRICULUM

Covers: Jenkins, Bamboo, TeamCity, GitHub Actions, GitLab CI, Azure DevOps. Hands-on labs and real-world scenarios.
Covers: Apache Maven, Gradle, Apache Ant, MSBuild, Makefile, NAnt, Grunt. Hands-on labs and real-world scenarios.
Covers: Nexus, Artifactory, NuGet, Chocolatey, APT, YUM, RPM, Apache Archiva. Hands-on labs and real-world scenarios.
Covers: Jira, Zendesk. Hands-on labs and real-world scenarios.
Covers: Python, Bash, PowerShell, Groovy, Ruby, Perl. Hands-on labs and real-world scenarios.

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