Managing software across hundreds or thousands of endpoints is one of the most persistent challenges for IT operations and MSPs. Manual installs, inconsistent versions, and user-driven updates create inefficiencies and security risks.
Chocolatey, a Windows-native package manager, combined with the Chocolatey for Automate plugin, provides a scalable, automated solution for software deployment and lifecycle management. This post outlines the technical benefits of using Chocolatey in conjunction with Automate, and how the plugin simplifies package management across unlimited agents.
What is Chocolatey?
Chocolatey is a package manager for Windows, built on NuGet and PowerShell. It enables:
- Silent installs and upgrades of thousands of applications.
- Scriptable workflows for configuration and deployment.
- Community and enterprise repositories with pre-built packages for common software.
- Consistency across environments, ensuring endpoints run approved versions.
Chocolatey functions much like apt-get or yum in Linux environments, but is tailored for Windows systems.
The Chocolatey for Automate Plugin
The plugin integrates Chocolatey directly into ConnectWise Automate, providing centralized control over package management. Key features include:
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Unlimited Agent Licensing
Manage software across unlimited endpoints without per-device costs. -
Global and Client-Level Consoles
Define sources, assignments, and approved packages at both global and client scopes. -
Proxy and Caching Support
Distribute packages via UNC shares or cloud caching servers to avoid rate-limit errors. -
WinGet Integration
Flexibility to use Microsoft’s WinGet alongside Chocolatey, depending on package availability. -
Automation via Groups and Searches
Version 3.7 shifted automation logic to Automate Groups and Searches, reducing load and improving scheduling efficiency. -
Enhanced Troubleshooting Tools
Improved logging and support for special characters in scripts.
Benefits for MSPs and IT Teams
Using Chocolatey with Automate delivers measurable operational improvements:
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Time Savings
Automate repetitive tasks such as installing browsers, updating conferencing tools, or patching utilities. -
Consistency and Compliance
Ensure endpoints run the same approved versions, reducing vulnerabilities and support incidents. -
Scalability
Manage environments ranging from dozens to thousands of endpoints without additional overhead. -
Client Satisfaction
Updates and installs occur silently in the background, minimizing disruption. -
Flexibility
Combine Chocolatey and WinGet depending on package availability or client requirements.
Example Workflow
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Define Packages
Select approved software packages from Chocolatey or WinGet repositories. -
Assign to Groups
Use Automate Groups to target specific clients, departments, or device types. -
Schedule Updates
Configure automation to run daily, weekly, or monthly. -
Monitor Logs
Review plugin logs and EDFs for success/failure reporting. -
Troubleshoot
Use enhanced logging and management tools to resolve package errors quickly.
Chocolatey provides the package management foundation, while the Chocolatey for Automate plugin delivers orchestration and scalability. Together, they transform software management from a manual, error-prone process into a streamlined, automated workflow suitable for MSPs and enterprise IT teams.
By adopting this combination, organizations gain consistency, efficiency, and control over their software environments—critical factors in modern IT operations.
