The problem

Install software on Windows and keep it updated is a boring and repetitive task.

Linux and BSD/OSX users can install software from packages and keep it updated with a simple apt-get update;apt-get upgrade command.

Wouldn’t it be great to have the same feature on Windows?

The automation

Chocolatey is a package manager for Windows fast to install, easy to use and supports thousands of software.

Installation is very simple, just one command:

@powershell -NoProfile -ExecutionPolicy Bypass -Command "iex ((new-object net.webclient).DownloadString(''))" && SET PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin

The initial (re)installation of the software I already use via chocolatey (if available) instead of the usual exe/msi installer worth the effort. Now I can upgrade all of them with just one command:

choco upgrade all -y

If you don’t like to use it from CLI there’s a GUI available.