Install Chocolatey on a Windows VPS

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.