Install Chocolatey on a Windows VPS - Documentation Infrawire

Chocolatey is a package manager for Windows, handy on a VPS to install or update software via the command line without clicking through multiple installers.

Prerequisites

Windows Server or recent Windows
PowerShell run as Administrator
Execution policy allowing the install script (see below)

Allow scripts (current session)

Open PowerShell (Admin):


PowerShell
Set-ExecutionPolicy Bypass -Scope Process -Force

Install Chocolatey

Still as administrator, run the official command (see chocolatey.org/install for updates):


PowerShell
[System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072
iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))

Close and reopen PowerShell, then verify:


PowerShell
choco -v

Example installs


PowerShell
choco install git -y
choco install 7zip -y
choco install vscode -y

Upgrade all Chocolatey packages:


PowerShell
choco upgrade all -y

Best practices

Use -y for non-interactive server deployments.
Install only what you need to reduce attack surface.
Document versions for production and test upgrades.

Troubleshooting

Access denied: ensure PowerShell is elevated.
Corporate proxy: configure system proxy or Chocolatey’s documented proxy options.

Chocolatey is a third-party ecosystem; verify package details on the community gallery before installing.