Chocolatey

Chocolatey is a Windows package manager that automates software installation, updates, and configuration. Manage packages directly from PowerShell or Command Prompt.

Installation

Bootstrap Chocolatey

# Run PowerShell as Administrator, then:
Set-ExecutionPolicy Bypass -Scope Process -Force; `
[System.Net.ServicePointManager]::SecurityProtocol = `
  [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; `
iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))

# Verify installation
choco --version

Using Windows Package Manager (Alternative)

winget install Chocolatey.Chocolatey

Basic Commands

Command	Description
choco --version	Display Chocolatey version
choco --help	Show general help
choco help <command>	Get specific command help
choco list	List all installed packages
choco search <package>	Search for package
choco install <package>	Install package
choco upgrade <package>	Upgrade package
choco uninstall <package>	Uninstall package

Installation Commands

# Install single package
choco install notepadplusplus

# Install multiple packages
choco install git nodejs python

# Install with version
choco install git --version=2.35.1

# Install without confirmation
choco install git -y

# Install to specific directory
choco install git --install-arguments="'INSTALLDIR=C:\Git'"

# Install with parameters
choco install nodejs --params="'/InstallDirectory:C:\nodejs'"

# Install from local package
choco install ./localpackage.nupkg

# Install from custom source
choco install package -s https://custom-feed.com

Search and Discovery

# Search for packages
choco search docker

# Search with detailed info
choco search nodejs --verbose

# List all packages in remote repository
choco list --page=0 --page-size=50

# Search local packages only
choco list --local-only

# Search with approved-only flag
choco search vim --approve-only

Package Management

# List installed packages
choco list

# List installed with version
choco list --local-only

# List outdated packages
choco outdated

# Get info about specific package
choco info python

# Show package dependencies
choco depends git

# Pin package (prevent upgrades)
choco pin add -n git

# Unpin package
choco pin remove -n git

Upgrade Operations

# Upgrade single package
choco upgrade git

# Upgrade multiple packages
choco upgrade nodejs python ruby

# Upgrade all packages
choco upgrade all

# Upgrade without confirmation
choco upgrade all -y

# Upgrade to specific version
choco upgrade git --version=2.35.1

# Upgrade with parameters
choco upgrade nodejs --params="'/SILENT'"

# Upgrade excluding specific packages
choco upgrade all --except="git,nodejs"

Uninstall and Cleanup

# Uninstall single package
choco uninstall notepadplusplus

# Uninstall multiple packages
choco uninstall git nodejs -y

# Uninstall with dependencies
choco uninstall packagename --remove-dependencies

# Uninstall forcing even if errors
choco uninstall git -f -y

# Remove package cache
choco cache list

# Clear all cache
rm $env:ChocolateyInstall\cache\*.nupkg

Configuration

# Show configuration
choco config list

# Set configuration value
choco config set cacheLocation D:\ChocolateyCache

# Set proxy
choco config set proxyLocation http://proxy.company.com:8080

# Set proxy user
choco config set proxyUser username

# Set default confirmation
choco config set confirmAll true

# Allow global confirmation
choco feature enable -n useRememberedArgumentsForUpgrades

Source Management

# List sources
choco source list

# Add source
choco source add -n=custom -s=https://my-nuget-feed.com

# Remove source
choco source remove -n=custom

# Disable source
choco source disable -n=custom

# Enable source
choco source enable -n=custom

# Set priority (order matters for resolution)
choco source list --verbose

Advanced Features

Feature Management

# List features
choco feature list

# Enable feature
choco feature enable -n=caskNuget

# Disable feature
choco feature disable -n=caskNuget

# Common features
choco feature list  # Shows: exitOnRebootDetected, autoUninstaller, etc.

Export and Import Packages

# Export installed packages
choco export packages.config

# Get package list as command
choco list | Select-Object -Property Name > packages.txt

# Convert list to install command
Get-Content packages.txt | ForEach-Object { "choco install $_ -y" }

# Create packages.config and import
# Manually create packages.config, then:
choco install packages.config -y

Batch Processing

# Install all packages from file
$packages = @("git", "nodejs", "python", "vscode", "7zip")
foreach ($package in $packages) {
    choco install $package -y
}

# Upgrade all with filter
choco upgrade all -y --except="dotnet-core,java"

# Uninstall with filter
Get-Item "$env:ProgramFiles\*" |
  Where-Object { $_.Name -match "OldApp" } |
  ForEach-Object { choco uninstall $_.Name -y }

Common Package Examples

# Developer Tools
choco install git nodejs python vscode visualstudio2022community

# Utilities
choco install 7zip winrar notepadplusplus vlc

# Browsers
choco install googlechrome firefox edge

# Communication
choco install discord slack

# Media
choco install ffmpeg imagemagick

# Virtual Machines
choco install virtualbox docker-desktop

# System Tools
choco install sysinternals ccleaner everything

# Languages
choco install golang rust ruby php

Scripting Examples

PowerShell Script to Install Development Environment

# dev-setup.ps1
param(
    [switch]$SkipConfirm
)

$packages = @(
    "git",
    "nodejs",
    "python",
    "vscode",
    "docker-desktop",
    "postman",
    "dbeaver",
    "mingw"
)

Write-Host "Installing development packages..."

if ($SkipConfirm) {
    foreach ($package in $packages) {
        choco install $package -y
    }
} else {
    foreach ($package in $packages) {
        choco install $package
    }
}

Write-Host "Development environment setup complete!"

Scheduled Update Script

# update-packages.ps1 (Run via Task Scheduler)
$logFile = "C:\Logs\choco-update.log"
$timestamp = Get-Date -Format "yyyy-MM-dd HH:mm:ss"

Add-Content -Path $logFile -Value "$timestamp - Starting package update"

try {
    choco upgrade all -y --limit-output
    Add-Content -Path $logFile -Value "$timestamp - Update successful"
} catch {
    Add-Content -Path $logFile -Value "$timestamp - Update failed: $_"
}

Troubleshooting

Clear Corrupted Cache

# Stop all choco processes
Stop-Process -Name "chocolatey*" -Force

# Clear cache directory
Remove-Item "$env:ChocolateyInstall\cache\*" -Force

# Reinstall problematic package
choco install packagename -f -y

Fix Installation Issues

# Reset Chocolatey environment
$env:ChocolateyInstall = 'C:\ProgramData\chocolatey'
$env:Path = "$env:ChocolateyInstall\bin;$env:Path"

# Fix permissions
icacls "C:\ProgramData\chocolatey" /grant:r "$env:username`:F" /t

# Verify installation
choco --version

Proxy Issues

# Set proxy
choco config set proxyLocation http://proxy:8080
choco config set proxyUser username
choco config set proxyPassword password

# Test connection
choco search chocolatey -s http://chocolatey.org

Best Practices

Maintenance Schedule

# Weekly: Check for outdated packages
choco outdated

# Monthly: Full system update
choco upgrade all -y

# Quarterly: Clean package cache
rm $env:ChocolateyInstall\cache\*.nupkg

Security Recommendations

• Keep Chocolatey updated: choco upgrade chocolatey -y
• Verify package sources from trusted repositories
• Use -f (force) flag cautiously
• Regularly update all packages: choco upgrade all
• Use Windows Defender for malware scanning

Performance Optimization

# Disable Windows Update during package operations
# Reduce explorer lock issues

# Use PowerShell's parallel execution for multiple packages:
@("git", "nodejs", "python") |
  ForEach-Object -Parallel {
    choco install $_ -y
  } -ThrottleLimit 3

Integration with CI/CD

GitHub Actions Example

name: Setup Windows Environment
jobs:
  setup:
    runs-on: windows-latest
    steps:
      - name: Install Chocolatey packages
        run: |
          choco install git nodejs python -y
          choco upgrade all -y

Azure DevOps Pipeline

jobs:
  - job: SetupEnvironment
    pool:
      vmImage: 'windows-latest'
    steps:
      - script: choco install git python nodejs -y
        displayName: Install packages

Resources

• Chocolatey Official Site
• Package Repository
• Documentation
• Community Forum
• GitHub Repository

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Last updated: 2025-03-30