If you are a Microsoft Windows user, there is a good chance you never heard of Chocolatey. If you are a Mac user, you may have heard of Brew which is a fairly similar solution.
Chocolatey is a package manager for Windows to make installing, removing, and updating software a breeze.
While Chocolatey is free, there is a paid annual license for more advanced features. Don't worry, you will likely be fine using the free version.
Why use Chocolatey?
Chocolatey allows you to easily install trusted versions of software and update them all at once.
Once you install Chocolatey, installing software is as simple as running the command choco install notepadplusplus. Most installations are completely done via the command prompt and no GUI windows are needed to complete the installation.
I recommend browsing https://chocolatey.org/packages to get a feel for the packages you can install. There are over 7,000 maintained packages the last time I checked.
Once you have a few packages installed with Chocolatey, you can just use choco update all to update them all at once.
The functionality of Chocolatey is very similar to Linux's apt and MacOS brew. This was something that was not available on Windows until Chocolatey came around.
The Pro version of Chocolatey is $96/year and covers up to 8 PCs on your network.
Out of all the Pro features, the malware scanning is the most attractive. The malware protection just uses the free site Virus Total to scan with over 50 virus scanners. That being said, Chocolatey packages are frequently managed by the community and anything out of order is dealt with quickly.
For most users, I don't see any demanding need to use the paid version.
Installing Chocolatey
Installation is really simple, but I will refer you to the official installation page for instructions.
Learning Chocolatey
I recommend checking out the offical courses page to get some hands-on with Chocolatey. Honestly, though, it doesn't take but 1-2 minutes to learn the basics. You can get pretty advanced with Chocolatey if you start using integrations.
Chris Titus has a great video that is under 10 minutes that will give you a great overview of using Chocolatey.
