What is Chocolatey?

Chocolatey or Choco as it is sometimes referred to, is a free, open-source package manager for Windows that is very similar to Apt or DNF in the Linux realm. In other words, this is a program used for installing software via the Windows command line. It downloads a program, installs it, then it will check for updates, and installs those updates automatically if needed. Those who use Linux are quite familiar with the package management systems like this.

Some ask, “Why should we choose to use a program like this, since we can simply download the .exe or .msi software and install the program ourselves?”

That is an excellent question. Here are several solid answers.

• When we install a new operating system and want to use numerous programs, we must look for each program installer, download it, install it, and then regularly check for updates. The Chocolatey package manager this all by itself, when using automatic mode.
• Instead of searching for an executable installer, we can install the program using the Chocolatey package manager and complete everything using the command line. It is much more convenient and faster.
• We can conveniently and more comfortably control the application versions we need. Most often, when we go to download an executable for the application, it downloads the latest version for us, and we do not always need the latest version.
• Chocolatey provides clear, simple commands which are almost identically used in all package management systems.

Prerequisites

• Windows 7 or later / Windows Server 2003 or later
• PowerShell v2 or later
• .NET Framework 4 or later

(As an aside, the installation will attempt to install .NET 4.0 if you do not have it already installed.)

Installation

Let’s move on to the installation. There are two options for installing Chocolatey. We can install Chocolatey via the command line or through PowerShell. The option to use cmd is most often used for Windows, and PowerShell for running scripts. In this case, we can run both cmd and PowerShell, but as an administrator, for this installation.

Install Using Powershell

When installing the software via PowerShell, we must ensure the local
Get-ExecutionPolicy
is not set to restricted. Chocolatey suggests using
Bypass
to bypass the policy to get things installed or
AllSigned
for increased security.

First, we need to run.
Get-ExecutionPolicy
If it returns
Restricted

Then we need to run
Set-ExecutionPolicy AllSigned
or
Set-ExecutionPolicy Bypass -Scope Process.

Now run the following command in the Windows shell.
Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))

If there are no errors, Chocolatey will be installed. We can verify the installation using one of the following commands.
choco
or
choco -?

Install Using Windows Cmd Shell

First, we need ensure that we are using an administrative shell.
Next, copy the following command to our cmd.exe shell.

@"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" -NoProfile -InputFormat None -ExecutionPolicy Bypass -Command " [System.Net.ServicePointManager]::SecurityProtocol = 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin"

And then press enter. 

The installation should look something like this.

Microsoft Windows [Version 10.0.18363.900]
(c) 2019 Microsoft Corporation. All rights reserved.
C:\WINDOWS\system32>@"%SystemRoot%\System32\WindowsPowerShell\v1.0\powershell.exe" -NoProfile -InputFormat None -ExecutionPolicy Bypass -Command " [System.Net.ServicePointManager]::SecurityProtocol = 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))" && SET "PATH=%PATH%;%ALLUSERSPROFILE%\chocolatey\bin"
Getting latest version of the Chocolatey package for download.
Getting Chocolatey from https://chocolatey.org/api/v2/package/chocolatey/0.10.15.
Extracting C:\Users\user\AppData\Local\Temp\chocolatey\chocInstall\chocolatey.zip to C:\Users\user\AppData\Local\Temp\chocolatey\chocInstall...
Installing chocolatey on this machine
Creating ChocolateyInstall as an environment variable (targeting 'Machine')
Setting ChocolateyInstall to 'C:\ProgramData\chocolatey'
WARNING: It's very likely you will need to close and reopen your shell
before you can use choco.
Restricting write permissions to Administrators
We are setting up the Chocolatey package repository.
The packages themselves go to 'C:\ProgramData\chocolatey\lib'
(i.e. C:\ProgramData\chocolatey\lib\yourPackageName).
A shim file for the command line goes to 'C:\ProgramData\chocolatey\bin'
and points to an executable in 'C:\ProgramData\chocolatey\lib\yourPackageName'.
Creating Chocolatey folders if they do not already exist.
WARNING: You can safely ignore errors related to missing log files when
upgrading from a version of Chocolatey less than 0.9.9.
'Batch file could not be found' is also safe to ignore.
'The system cannot find the file specified' - also safe.
WARNING: Not setting tab completion: Profile file does not exist at
'C:\Users\user\Documents\WindowsPowerShell\Microsoft.PowerShell_profile.ps1'.
Chocolatey (choco.exe) is now ready.
You can call choco from anywhere, command line or powershell by typing choco.
Run choco /? for a list of functions.
You may need to shut down and restart powershell and/or consoles
first prior to using choco.
Ensuring chocolatey commands are on the path
Ensuring chocolatey.nupkg is in the lib folder
C:\WINDOWS\system32>

Verify Installation

To verify that Chocolatey is installed, we will use the choco command.

C:\WINDOWS\system32>choco
Chocolatey v0.10.15
Please run 'choco -?' or 'choco -?' for help menu.

C:\WINDOWS\system32>

Excellent! Chocolatey is installed!

Basic Chocolatey Commands

Now let’s review some of the basic commands for using Choco. Choco commands can be used in both the Windows cmd shell and in PowerShell.

Install Program

To install a specific program, use the following command.
choco install <pkg|packages.config> [ ] []</pkg|packages.config>

For example:
choco install chrome

For a complete listing of install options, visit the Choco install page or run the following command.
choco install -h

Update Program

To update a program, we will use the following command.
choco upgrade <pkg|all> [ ] []</pkg|all>
For example:
сhoco upgrade chrome

Update All Programs

To update all programs, we need to use the following command.
cup <pkg|all> [ ] []</pkg|all>
or
choco upgrade all

If you noticed, the cup command is an alternative to using the choco upgrade command.

Search For a Program

To find a needed program for downloading and installation, we can enter the following command.
choco search chrome

See Installed Programs

Using the following command, you can see which programs are already installed using Choco.
choco list --local-only
Chocolatey v0.10.15
chocolatey 0.10.15
chocolatey-core.extension 1.3.3
kubernetes-cli 1.18.2
Minikube 1.10.1
vscodium 1.38.0
5 packages installed.

C:\WINDOWS\system32>

Update Chocolatey

We can update the Choco program itself using this command.
choco upgrade chocolatey

It is important to do this periodically because in previous versions, errors may be detected, and they need to be fixed so that there are no vulnerabilities.

Install the Chocolatey GUI

If someone is not comfortable using the command line, we can install the graphical user interface of Chocolatey using this command.
choco install chocolateygui

Conclusion

That’s it! As you can see, using Chocolatey is very simple. Overall, we have found that Chocolatey is an excellent tool in our local systems administration toolbox. It is reliable, definitive, and consistently updated. Overall, it is an exceptional product.