How to Install and Use Chocolatey Package Manager on Windows Server 2025

How to Install and Use Chocolatey Package Manager on Windows Server 2025

Chocolatey is the most widely-used open-source package manager for Windows, bringing the Linux apt / yum experience to the Windows ecosystem. It allows system administrators to install, upgrade, and remove software from the command line, script entire server configurations with a single PowerShell file, and maintain consistent, auditable software inventories across fleets of servers. On Windows Server 2025, Chocolatey is particularly valuable for automating base server builds — installing developer tools, runtimes, monitoring agents, and utilities without ever clicking through a wizard. This guide covers installing Chocolatey, using it for day-to-day package management, building a custom package, and setting up an internal feed for air-gapped environments.

Prerequisites

• Windows Server 2025 with an administrator account
• PowerShell 5.1 or PowerShell 7.x (run as Administrator)
• Internet access to chocolatey.org, or an internal Nexus/Artifactory mirror
• Execution policy that allows running scripts (the installer handles this temporarily)
• .NET Framework 4.8 (pre-installed on Windows Server 2025)

Step 1: Install Chocolatey

The official one-liner installs Chocolatey by downloading and executing the installation script from chocolatey.org. Run PowerShell as Administrator before proceeding:

# Temporarily bypass execution policy to allow the installer to run
Set-ExecutionPolicy Bypass -Scope Process -Force

# Set TLS 1.2 to ensure secure download
[System.Net.ServicePointManager]::SecurityProtocol = `
    [System.Net.ServicePointManager]::SecurityProtocol -bor 3072

# Download and run the Chocolatey install script
Invoke-Expression ((New-Object System.Net.WebClient).DownloadString(
    'https://community.chocolatey.org/install.ps1'
))

After installation, close and reopen PowerShell so the PATH is reloaded, then verify:

choco --version
# 2.x.x

# View Chocolatey environment info
choco config list

Chocolatey installs to C:ProgramDatachocolatey and adds this directory to the system PATH.

Step 2: Install, Uninstall, and Upgrade Packages

The core Chocolatey commands mirror familiar Linux package manager syntax:

# Install a single package (accepts license prompts automatically with -y)
choco install git -y

# Install a specific version
choco install nodejs --version=20.19.1 -y

# Install multiple packages in one command
choco install 7zip notepadplusplus googlechrome -y

# Install silently with no progress bars (good for scripts)
choco install git -y --no-progress

# Uninstall a package
choco uninstall git -y

# Upgrade a specific package to its latest version
choco upgrade nodejs -y

# Upgrade ALL installed Chocolatey packages
choco upgrade all -y

# Upgrade all packages — dry run (see what would change without doing it)
choco upgrade all --noop

Step 3: Search for and List Packages

# Search the Chocolatey Community Repository
choco search python

# Search with version details
choco search python --all-versions

# List all locally installed Chocolatey packages
choco list --local-only

# Short form (equivalent)
choco list -l

# Show which packages have newer versions available
choco outdated

# Get detailed info about a specific package
choco info nodejs

Step 4: Install the Chocolatey GUI

For administrators who prefer a graphical interface, Chocolatey GUI provides a Windows desktop application for browsing, installing, and managing packages:

# Install Chocolatey GUI
choco install chocolateygui -y

# Launch it
Start-Process chocolateygui

Chocolatey GUI displays installed packages, available updates, and lets you search the community repository with filtering and sorting. It also shows package details, screenshots, and release notes.

Step 5: Create a Custom Chocolatey Package

You can package any software — including internal applications — as a Chocolatey package. A package consists of a .nuspec metadata file and a chocolateyInstall.ps1 script.

# Create a new package scaffold
choco new MyInternalApp

# This creates the directory structure:
#   MyInternalApp/
#     MyInternalApp.nuspec
#     tools/
#       chocolateyInstall.ps1
#       chocolateyUninstall.ps1  (optional)

Edit MyInternalApp.nuspec:

<?xml version="1.0" encoding="utf-8"?>
<package xmlns="http://schemas.microsoft.com/packaging/2015/06/nuspec.xsd">
  <metadata>
    <id>MyInternalApp</id>
    <version>1.4.2</version>
    <title>My Internal App</title>
    <authors>Corp IT</authors>
    <description>Internal order processing application.</description>
    <tags>internal corp</tags>
  </metadata>
</package>

Edit toolschocolateyInstall.ps1:

$ErrorActionPreference = 'Stop'

$packageArgs = @{
    packageName    = 'MyInternalApp'
    fileType       = 'msi'
    url64bit       = 'https://intranet.corp.example.com/packages/MyInternalApp-1.4.2-x64.msi'
    checksum64     = 'A1B2C3D4E5F6...'
    checksumType64 = 'sha256'
    silentArgs     = '/quiet /norestart'
    validExitCodes = @(0, 3010)
}

Install-ChocolateyPackage @packageArgs

Build the package into a .nupkg file:

Set-Location "C:choco-packagesMyInternalApp"
choco pack

# Output: MyInternalApp.1.4.2.nupkg

Step 6: Set Up an Internal Chocolatey Feed with Nexus

For air-gapped environments or when you need to control which packages are available, host an internal NuGet feed using Nexus Repository Manager or Artifactory:

# Install Nexus OSS via Chocolatey
choco install nexus-repository -y

# Start the Nexus service
Start-Service -Name "nexus"

# Default Nexus URL: http://localhost:8081
# Default admin credentials: admin / (check C:ProgramDatasonatype-worknexus3admin.password)

In the Nexus web UI:

1. Create a new NuGet (hosted) repository named chocolatey-internal.
2. Create a new NuGet (proxy) repository pointing to https://community.chocolatey.org/api/v2/.
3. Create a NuGet (group) repository that combines both.

Configure Chocolatey to use your internal feed:

# Remove the default community source
choco source remove --name="chocolatey"

# Add your internal Nexus group feed
choco source add `
    --name="nexus-internal" `
    --source="http://nexus.corp.example.com:8081/repository/chocolatey-group/api/v2" `
    --user="choco-consumer" `
    --password="ChangeMe123" `
    --priority=1

# Verify sources
choco source list

# Push your custom package to the internal hosted repo
choco push "MyInternalApp.1.4.2.nupkg" `
    --source="http://nexus.corp.example.com:8081/repository/chocolatey-internal/api/v2" `
    --api-key="YOUR_NEXUS_API_KEY"

Step 7: Automate Server Builds with a Packages Script

Define your entire server software baseline in a single PowerShell script that can be run on any fresh Windows Server 2025 installation:

# server-baseline.ps1
# Run as Administrator

# Ensure Chocolatey is installed
if (-not (Get-Command choco -ErrorAction SilentlyContinue)) {
    Set-ExecutionPolicy Bypass -Scope Process -Force
    [System.Net.ServicePointManager]::SecurityProtocol = 3072
    Invoke-Expression ((New-Object System.Net.WebClient).DownloadString(
        'https://community.chocolatey.org/install.ps1'
    ))
}

# Core tools
choco install 7zip git notepadplusplus -y

# Runtimes
choco install nodejs --version=20.19.1 -y
choco install dotnet-8.0-runtime -y

# Monitoring and management
choco install sysinternals -y
choco install openssh -y

Write-Host "Server baseline installation complete." -ForegroundColor Green

Conclusion

Chocolatey transforms Windows Server 2025 software management from a manual, GUI-driven process into a scriptable, repeatable, and auditable operation. Whether you are bootstrapping a new server, maintaining a consistent software inventory across dozens of machines, or distributing internal applications through a private Nexus feed, Chocolatey provides the tooling to do it efficiently. Combined with an internal repository for air-gapped environments and a baseline install script committed to source control, you can rebuild any server to a known good state in minutes rather than hours.