How to Use Chocolatey to Easily Install and Update Windows Programs

Chocolate Feature

If you have enough Windows programs that keeping them all updated seems like a bit of a chore, it might be time to start making the switch over to a package manager, specifically Chocolatey.

Package managers are a little like app stores in that they allow you to manage and update all of your programs through a single interface rather than having to wrangle them all individually. For a time, Chocolatey was only available through the command line, which limited its potential audience to people who weren’t scared off by that, but its GUI has been getting steadily better, making it accessible to just about anyone.

Installing Chocolatey and ChocolateyGUI

Okay, you do have to use the command line a little bit to get Chocolatey up and running, but after that, it’s GUI all the way. They have instructions on their website, which you may need to refer to if you don’t have administrative rights on your machine, but the following steps should work for most people with Windows 7 or above.

I’m using the Powershell instructions here, as I’ve found they work more reliably than the cmd method, but both methods are explained pretty well on the Chocolatey site.

1. Open an administrative shell. The easiest way to do this is pressing Win + X and selecting Windows Powershell (Admin).

Chocolatey Powershell Install 1

2. Next, paste in Get-ExecutionPolicy and hit Enter. If you see it return “Restricted,” you can paste in Set-ExecutionPolicy AllSigned or Set-ExecutionPolicy Bypass -Scope Process. Either one works.

Chocolatey Install Powershell 1 Execution Policy

3. Now you’ll need to paste in the install command:

Set-ExecutionPolicy Bypass -Scope Process -Force; iex ((New-Object System.Net.WebClient).DownloadString(''))
Chocolatey Install Powershell 2 Install

You’ll see some installation text scroll by. Once it’s finished, you’re good to go! Chocolatey is installed and now commands like choco install and choco upgrade will allow you to manage programs in the command line (cmd or Powershell). If you want to stick to the GUl, though, you’ll only have to mess around with the nerdy stuff one more time.

Chocolatey Install Powershell 3 Finished

4. In the Powershell admin window, type or paste in

choco install chocolateygui
Chocolatey Gui Install 3 Powershell

This will start downloading and installing the GUl program you’ll need to visually manage Chocolatey. You’ll need to select Y to finalize the installation. If you don’t want to be bothered by this again in the future, you can type in

choco feature enable -n allowGlobalConfirmation

Your ChocolateyGUI is now installed, and your command line days are now behind you, if you want them to be!

Installing programs with ChocolateyGUI

To open ChocolateyGUI, find the program on your desktop or in your Start menu and launch it.

Once you’re in the program, you’ll see two main tabs on the left: “This PC” and “chocolatey.” “This PC” allows you to manage the programs you’ve installed via Chocolatey, and “chocolatey” allows you to search for programs you want to install. Any programs you’ve installed without using Chocolatey will not show up here. You’ll have to reinstall them or get Chocolatey to take them over.

Chocolatey Gui Chocolatey

The Chocolatey program listing shows up as a list by default, organized by the programs’ popularity, but the tile layout arguably makes for more efficient browsing. You can change that using the buttons in the top-right corner. Browsing manually might get a little bit slow, though, so use the search bar to hunt for specific programs.

Chocolatey Gui Search

When you find the program you want, you can either check out more details on it or go straight to installing. Once you click install (choco install [program]), your program should set up pretty much on its own.

Chocolatey Gui Install 2 Teracopy

After the dialog is finished, you’ll find your new program in your start menu with all the others.

Updating programs with ChocolateyGUI

Installing programs is easier with Chocolatey, but the update feature is where things get really awesome. ChocolateyGUI makes it very easy to see which of your programs are out of date, and getting them all up to speed just takes a few clicks.

Chocolatey Gui Update 1

If you just want to update one, you can right-click it and select “Update” (choco upgrade [program]). That’s already easier than a lot of programs make it, but the best thing is that you don’t have to go one by one. The refresh symbol with an asterisk in the menu on the top right means “Update All,” and if you press it, Chocolatey will automatically update every program in its list. Alternatively, use choco upgrade all in the command line. Updating your programs can now be a once-a-week task that just takes a few clicks.

Making the move to package management

Odds are that you already have most of the programs you use on a daily basis installed, and you probably did it by downloading and setting up each one, unless you got it through the Microsoft Store, which is at least a nod to getting package management set up in Windows. Making the switch to Chocolatey might be a little annoying then, since you’ll have to use it to reinstall the programs you already have or take over existing installs. But if you just turn to Chocolatey every time, you would have otherwise downloaded and run an .exe or .msi, you would eventually end up with a lot of your programs under the Chocolatey umbrella.

Even better: when you’re setting up a new computer you can use some command line tricks for batch installations, meaning a few minutes of typing could get your computer set up with every program you want, all manageable via Chocolatey. This, combined with how easy it will be to update your programs now, leaves you plenty of time to be a nerd about something else. You’ve earned it.

Andrew Braun
Andrew Braun

Andrew Braun is a lifelong tech enthusiast with a wide range of interests, including travel, economics, math, data analysis, fitness, and more. He is an advocate of cryptocurrencies and other decentralized technologies, and hopes to see new generations of innovation continue to outdo each other.

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