2025 Comparison - Microsoft Windows CLI Tools

🧭 Why Package Managers on Windows?

On Linux, using package managers like apt, dnf, zypper or pacman has become second nature for installing, updating and managing software. On Windows, the convenience of launching executables (.exe, .msi) with a simple click was a relief for users.

Today, SafeITExperts reveals: Windows also has command-line tools: winget, Chocolatey and Scoop. Let's explore them together.

On Linux, package managers are central:

Windows bridges the gap with winget (official), Chocolatey (DevOps veteran) and Scoop (minimalist, no admin). 🎯

💻 Accessing the Shell: PowerShell, CMD & Terminal

Which shell to use?

• PowerShell (recommended): Modern shell with powerful scripting language.
• CMD: Legacy command interpreter (works, but less comfortable).
• Windows Terminal: Application that can host PowerShell, CMD, WSL/Bash, etc.
• PowerShell 7 (Core): Cross-platform version (parallel to PowerShell 5.x "Windows PowerShell").

How to open PowerShell

• Via Start menu: type "PowerShell", then "Run as administrator" for elevated session.
• Shortcut: Win + X → "Windows Terminal (Admin)" or "Windows PowerShell (Admin)".
• Run: Win + R → powershell → Enter (non-elevated).

Admin rights, password and UAC

On Windows, we don't type sudo. System actions trigger UAC (User Account Control):

• If your session has admin rights, you'll see a dialog box to confirm
• If your session is standard, you'll be prompted for admin credentials

winget/choco may require elevated sessions for "machine-wide" installations. Scoop works by default without admin (in user profile), but can also install globally with admin.

# Check & relax for current user
Get-ExecutionPolicy
Set-ExecutionPolicy -Scope CurrentUser RemoteSigned

🐧 WSL - Complete Linux Environment on Windows

Overview

Windows Subsystem for Linux (WSL) was created by Microsoft and introduced in 2016 to bring Windows and Linux closer together. WSL allows running a full GNU/Linux distribution (Ubuntu, Debian, Fedora, openSUSE, Kali…) directly on Windows, without heavy virtual machines or dual-boot.

• Concept: Real Linux kernel embedded in a lightweight Hyper-V VM
• Native access to Linux commands and packages (bash, apt, yum, pacman…)
• Transparent interoperability Windows ↔ Linux files (/mnt/c)
• Distributions: Available via Microsoft Store or WSL CLI (Ubuntu, Debian, Fedora…)
• Security:
  • Linux kernel provided and updated by Microsoft
  • Lightweight Hyper-V isolation
  • Admin rights only for initial installation

⚙️ WSL Installation

dism.exe /online /enable-feature /featurename:Microsoft-Windows-Subsystem-Linux /all /norestart
dism.exe /online /enable-feature /featurename:VirtualMachinePlatform /all /norestart
wsl --set-default-version 2
wsl --install -d Ubuntu
wsl --list --online
wsl --list --verbose

🛠️ Alternative Installation via Managers

# With winget
winget install --id Microsoft.WSL -e --source winget
wsl --install

# With Chocolatey
choco install wsl -y
wsl --install

# With Scoop (after Scoop installation)
scoop install sudo
sudo dism.exe /online /enable-feature /featurename:Microsoft-Windows-Subsystem-Linux /all /norestart
sudo dism.exe /online /enable-feature /featurename:VirtualMachinePlatform /all /norestart
wsl --install

🗣️ Voice Installation via Copilot

# Open Windows Terminal, activate Copilot (Win + C), and say:
"Install and configure WSL 2 with Ubuntu"
# Copilot will execute necessary commands

🔧 Distribution Management

wsl --list --verbose
wsl --set-version <distro> 2
wsl --terminate <distro>

🔎 Integration & Interoperability

ls /mnt/c/Users
cmd.exe /c dir C:\
wsl uname -r

📦 Linux Package Management

sudo apt update && sudo apt upgrade
sudo apt install <package>
sudo apt install <package>=<version>

🪟 winget - Windows Package Manager (Microsoft) official

Overview

winget is the official Windows package manager (Windows Package Manager), introduced by Microsoft. It allows installing, updating, configuring and uninstalling software directly from command line, similar to apt on Linux or brew on macOS.

• Origin: Microsoft (integrated in Windows 11, available on Windows 10 via "App Installer")
• Repositories (sources):
  • winget: Community repository maintained by Microsoft (manifests on GitHub)
  • msstore: Microsoft Store (packaged and signed apps via Store)
  • Private sources possible (enterprise)
• Security: Reviewed YAML manifests (automatic + human), SHA256 for installers, downloads from publisher sources

🔎 Search & Show

winget --version
winget search vscode
winget search --id Microsoft.VisualStudioCode -e
winget show Microsoft.VisualStudioCode

📦 Install

winget install --id Microsoft.VisualStudioCode -e
winget install --id Microsoft.VisualStudioCode -e --version 1.80.0
winget install --id Microsoft.VisualStudioCode --scope user
winget install --id Microsoft.VisualStudioCode --silent
winget install --id Microsoft.VisualStudioCode --override "/VERYSILENT /NORESTART"
winget install --id 9NBLGGH4NNS1 --source msstore

⬆️ Updates

winget upgrade
winget upgrade <name>
winget upgrade --all
winget upgrade --include-unknown

🧹 List / Uninstall / Export

winget list
winget uninstall --id Microsoft.VisualStudioCode -e
winget export -o apps.json --include-versions
winget import -i apps.json

📌 Pin, Sources & Configuration

winget pin add --id Microsoft.VisualStudioCode --version 1.80.*
winget pin list
winget pin remove --id Microsoft.VisualStudioCode

winget source list
winget source update
winget source reset

winget settings
winget features

🍫 Chocolatey - The DevOps/Enterprise Veteran

Overview

Chocolatey is one of the oldest Windows package managers (2011). Inspired by apt-get, automation/DevOps oriented, and widely used in enterprise environments.

• Origin: 2011, community + enterprise offering (C4B)
• Public repository: community.chocolatey.org/packages (NuGet)
• Private repositories: Heavily used in enterprise (Artifactory, Nexus, UNC share, etc.)
• Security:
  • Community-submitted packages
  • Human and automatic review before publication
  • Some scripts download from external sources (less strict than winget)
  • Chocolatey for Business version offers private repositories + enhanced verification

⚙️ Chocolatey Installation

Set-ExecutionPolicy Bypass -Scope Process -Force
[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
iex ((New-Object Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
choco --version

🔎 Search, List, Outdated

choco search vscode
choco list --localonly
choco outdated

📦 Install / Upgrade / Uninstall

choco install vscode -y
choco install vscode --version=1.80.0 -y
choco install nodejs-lts --pre -y
choco upgrade vscode -y
choco upgrade all -y
choco uninstall vscode -y

⬇️ Downgrade & Pin

choco install vscode --version=1.79.0 -y
choco pin add -n=vscode -v=1.79.0
choco pin list
choco pin remove -n=vscode

✅ Advantage: supports downgrade (rollback possible if version available).

🧩 Sources, Config, Features, Maintenance

choco source list
choco source add -n=myfeed -s "https://my.nexus/nuget/choco"
choco source disable -n=chocolatey

choco config get cacheLocation
choco config set cacheLocation "D:\ChocoCache"

choco feature list
choco feature enable -n=allowGlobalConfirmation

choco clean -y
choco upgrade all --noop

🗂️ Scoop - Minimalist, No Admin by Default

Overview

Scoop was created by Luke Sampson in 2013. It adopts a minimalist philosophy, close to the brew experience on macOS. Everything is installed in the user folder without requiring administrator rights.

• Concept: Installs apps in user profile (no UAC, no admin)
• Repositories: buckets (Git repositories):
  • Main repository: main
  • Additional buckets: extras, versions, nerd-fonts, Games, etc.
  • User can add custom buckets
• Security:
  • Buckets on GitHub, open contributions
  • SHA256 verification to ensure binaries aren't modified
  • More community-driven than winget, strongly depends on maintainers' rigor

⚙️ Scoop Installation

Set-ExecutionPolicy RemoteSigned -Scope CurrentUser
iwr -useb get.scoop.sh | iex
scoop --version

🪣 Buckets

scoop bucket list
scoop bucket known
scoop bucket add extras
scoop bucket add versions
scoop bucket rm extras

🔎 Search & Info

scoop search vscode
scoop info vscode
scoop list

📦 Install / Versions / Global

scoop install vscode
scoop install vscode@1.80.0
scoop install -g 7zip

⬆️ Update / Status

scoop update
scoop update vscode
scoop update *
scoop status

🔁 Change/Freeze Version & Maintenance

scoop reset vscode@1.79.0
scoop hold vscode
scoop unhold vscode
scoop cleanup vscode
scoop cleanup *
scoop checkup
scoop cache show
scoop cache rm *
scoop which code

scoop install aria2
scoop config aria2-enabled true

🤖 Copilot - AI Assistant for PowerShell and CLI Tools

Overview

Windows Copilot, integrated in Windows 11, revolutionizes CLI tool usage by acting as an intelligent voice and text assistant. It translates your natural language requests into precise PowerShell commands to interact with winget, Chocolatey and Scoop.

• Activation: Copilot button in taskbar or Win+C
• Key Features: Voice translation, script generation, error diagnosis
• Security: Confirmation before execution (except silent mode), command history

🎙️ Voice Commands with Copilot

# Install Docker with Winget silently
"Copilot, install Docker with winget without confirmation"
→ winget install Docker.DockerDesktop --silent

# Migrate my Chocolatey apps to Winget
"Copilot, migrate my Chocolatey apps to winget"
→ Automatic migration script

# Diagnose an installation error
"Copilot, why did Node.js installation fail?"
→ Log analysis and fix suggestions

⚡ Advanced Automation

Copilot generates scripts combining multiple tools:

# Multi-tool batch installation
"Copilot, install Git, Python and VS Code with the optimal tool"
→ winget install Git.Git Python.Python Microsoft.VisualStudioCode

# Cross-tools cleanup
"Copilot, clean unused packages on all managers"
→ scoop cleanup * & choco remove --all-versions & winget uninstall --orphaned

# Custom script
"Copilot, create a script that installs Java, clones my repo and runs the build"
→ Generation of a complete PowerShell script

🔧 Integration with Windows Tools

💡 Innovative Use Cases

# Compare installation performance
"Copilot, which tool is fastest to install 20 apps?"
→ Benchmark winget vs choco vs scoop

# Secure an installation
"Copilot, check if this Scoop script is safe before execution"
→ Potential risk analysis

# Complex dependency management
"Copilot, install Node.js with npm and configure PATH"
→ Installation + environment configuration

📊 Quick Comparison

🔒 Repositories & Security: How Do These Tools Compare to Linux?

Key Takeaways

• Linux: Integrated packages, signed, reproducible in distro-managed repos.
• Windows: These tools orchestrate publisher installers; trust chain relies on manifests, checksums, and binary provenance (official site, Store).
• In Enterprise: Prefer private repos (winget private source, Chocolatey feed, private Scoop buckets) and a validation process.

📚 Cookbook - Common Tasks (with Linux Analogies)

🛡️ Security & Best Practices

• Reliable Sources: Microsoft Store for winget when possible, official publisher URL.
• Checksums: Essential for Chocolatey; SHA256 manifests for winget and Scoop.
• Least Privilege: User scope (--scope user / Scoop by default).
• Private Repos in enterprise + validation pipeline (internal mirror).
• Export / Backup your stack (winget export; Scoop list; Choco via scripts).
• WSL: Keep kernel updated via Windows Update.

🎯 Practical Scenarios

1) Personal PC, Simple and Safe

• winget by default (integrated, reliable msstore source)
• Use --id and -e (exact) to avoid name collisions
• Export your selection:
  Copy

  winget export -o apps.json --include-versions

2) Dev Workstation (Flexible, No Admin)

• Scoop for CLI tools, multiple versions and easy cleanup
• WSL for complete Linux environment
• Enable aria2 to speed up downloads:
  Copy

  scoop install aria2
  scoop config aria2-enabled true

3) Enterprise / CI/CD

• Chocolatey + Private Repository (NuGet, Nexus, Artifactory)
• Require checksums, disable public repo, internal creation/review pipelines
• Pre-deployment simulation:
  Copy

  choco upgrade all --noop

❓ Frequently Asked Questions (FAQ)

Is a password required to use these commands?
Not in command line. If an action requires admin rights, Windows displays a UAC prompt: you confirm (admin session) or enter admin credentials if you're in a standard account.

Can I do everything from CMD?
Yes for winget and choco. Scoop mainly targets PowerShell. Windows Terminal is the most comfortable.

Is this as "secure" as Linux?
The model is different. Linux compiles and signs packages within official repositories. On Windows, these tools orchestrate publisher installers; security relies on manifests, hashes, publisher signatures (Store) and your policies (private repos in enterprise).

Can I use multiple managers on the same machine?
Yes, it's possible and sometimes recommended. For example: winget for main applications, Scoop for dev tools without admin rights. Just avoid installing the same software via multiple managers.

How to verify package integrity before installation?
- Winget: uses SHA256 hashes in official manifests
- Chocolatey: ensure package has valid checksums (avoid --allow-empty-checksums)
- Scoop: manifests include SHA256 hashes for each downloaded file

What's the best solution for deployment automation?
Chocolatey is best suited for enterprise environments with private repositories, approval features and SCCM/Intune integration. Winget is also becoming a strong option with its export/import features.

Does WSL replace Windows package managers?
No, WSL is complementary. It allows running complete Linux environments (with apt, dnf, etc.) while winget/choco/scoop manage Windows applications. You can use both together.

🎯 Conclusion

• winget: Default choice, integrated and reliable (especially with msstore source)
• Chocolatey: Very rich for automation and enterprise (downgrade, pin, private repos)
• Scoop: Lightweight and flexible, perfect without admin rights, multi-versions, easy cleanup
• Copilot: Revolutionary AI assistant to automate your CLI workflows
• WSL: Essential solution to run a complete Linux environment on Windows

For a "classic" Windows user, start with winget.
For machine fleets and DevOps, Chocolatey shines.
For devs/power-users, Scoop and WSL are essential.
For everyone, Copilot transforms your CLI experience.