3 minute read


Recently, I have got a new laptop and decided to get all new software with the scripts – to avoid clicking and downloading stuff manually. I have heard about Chocolatey in the past but had no opportunity to use it. A new laptop was a great excuse to play with some chocolate.

What is chocolatey?

Everyone I know loves chocolate, so in my mind, you cannot go wrong with anything choco-. Here is what they say about themselves on their website;

Chocolatey is a software management solution that gives you the freedom to create a simple software package and then deploy it anywhere you have Windows using any of your familiar configuration or system management tools. Designed to be simple to use, it provides a suite of powerful features that scale for your existing, and your future infrastructure. Power and flexibility in one simple product, that’s Chocolatey.

Install chocolatey

The official guide can be found here, as well as extensive installation course. If you are in a hurry, just follow this quick steps:

# Run Get-ExecutionPolicy. If it returns Restricted, then run Set-ExecutionPolicy AllSigned or Set-ExecutionPolicy Bypass -Scope Process.
PS C:\> Get-ExecutionPolicy

# Bypass. Nothing is blocked and there are no warnings or prompts.
PS C:\> Set-ExecutionPolicy Bypass -Scope Process -Force

# Now run the following command:
PS C:\> [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))
Getting latest version of the Chocolatey package for download.
Getting Chocolatey from https://chocolatey.org/api/v2/package/chocolatey/0.10.15.
Downloading 7-Zip commandline tool prior to extraction.
Extracting ...
Installing chocolatey on this machine

# confirm the choco is in the house
PS C:\> choco -v

Install packages

Great, you have got yourself some new shiny tool. What now? How to get other stuff?

One way would be to go to the Chocolatey library and search for your package.

There is a way to get that list via PowerShell too:

PS C:\> choco list

Once you find what you need, there is an easy way to install the packages.

# This is just a sample from my build.
PS C:\> choco install slack -y
PS C:\> choco install docker-desktop -y
PS C:\> choco install grammarly -y
PS C:\> choco install sql-server-management-studio -y
PS C:\> choco install greenshot -y
PS C:\> choco install opera -y
PS C:\> choco install vscode -y
# There are even some vscode extensions
PS C:\> choco install vscode-powershell -y
PS C:\> choco install vscode-gitlens -y
PS C:\> choco install vscode-docker -y

# to see the installed packages run (note the -localonly switch)
PS C:\> choco list -localonly

You have probably noticed that switch at the end -y, and here is the reason :

The package putty.install wants to run 'chocolateyInstall.ps1'.
Note: If you don't run this script, the installation will fail.
Note: To confirm automatically next time, use '-y' or consider:
choco feature enable -n allowGlobalConfirmation

Upgrade packages

Getting newer version of the packages or even chocolatey itself is very easy too.

# upgrade multiple packages at once
PS C:\> choco upgrade greenshot grammarly -y
<# One package was already on the latest version
Chocolatey upgraded 1/2 packages. 
 See the log for details (C:\ProgramData\chocolatey\logs\chocolatey.log).

# to upgrade chocolatey run
PS C:\> choco upgrade chocolatey -y

Uninstall packages

Removing packages follow the same pattern.

# it is good to have a package installed, when showing how to uninstall it
PS C:\> choco uninstall putty.install

<# otherwise...
Uninstalling the following packages:
putty.install is not installed. Cannot uninstall a non-existent package.

after a “fix” it should look like that

putty.install v0.73
 Running auto uninstaller...
 Auto uninstaller has successfully uninstalled putty.install or detected previous uninstall.
 putty.install has been successfully uninstalled.

Chocolatey uninstalled 1/1 packages. 
 See the log for details (C:\ProgramData\chocolatey\logs\chocolatey.log).

Some issues

Since it was my first time with Chocolatey I observed some issues, but so far only two were noticeable enough to make a note. The first one was a missing -y switch, which is not a typical issue but stopped me for a while.

The other thing is that Chocolatey sometimes stalls for a long time. Like a really long time. At some point, after waiting 30 minutes I had to kill the choco process and that helped.

More information

While I was doing my research on this subject I have found few interesting resources:

List of the parameters with descriptions in a short form. Kendra’s Kendra Little (blog|twitter) blog post about Installing Redgate SQL Toolbelt with Chocolatey + some interesting links and Chocolatey GUI.

Thank you,