Choco upgrade, y’all

Chocolatey is a package manager for Windows, like the built-in package managers on Linux, and third-party ones on macOS like Homebrew and MacPorts.

The idea is this: when you’re setting up a machine, you don’t want to have to think about which applications you need installed to get up and running. This could be a server or a development workstation, possibly even a gaming rig. Chocolatey provides an easy way to get a machine configured the way you want it, and fast too.

For example, on my development machine I have the following Chocolatey packages installed (using the command choco list -localonly). While this seems like A Lot™ — as the kids say — a fair number of these packages are dependencies which are installed automatically. The KB (short for Microsoft Knowledge Base) packages are a great example of this.

• 7zip 21.7
• 7zip.install 21.7
• adobereader 2022.001.20085
• autohotkey.portable 1.1.33.10
• choco-cleaner 0.0.8.4
• chocolatey 1.1.0
• chocolatey-core.extension 1.3.5.1
• chocolatey-dotnetfx.extension 1.0.1
• chocolatey-visualstudio.extension 1.10.0
• chocolatey-windowsupdate.extension 1.0.4
• chocolateygui 1.0.0
• curl 7.82.0
• dotnet-5.0-sdk-1xx 5.0.104
• dotnet-5.0-sdk-2xx 5.0.212
• dotnet-6.0-sdk 6.0.201
• dotnet-6.0-sdk-1xx 6.0.103
• dotnet-6.0-sdk-2xx 6.0.201
• dotnet-sdk 6.0.201
• DotNet4.5.2 4.5.2.20140902
• DotNet4.6.1 4.6.01055.20170308
• dotnet4.7.1 4.7.2558.20190226
• dotnet4.7.2 4.7.2.20210903
• dotnetcore-3.1-sdk 3.1.417
• dotnetcore-3.1-sdk-4xx 3.1.417
• dotnetcore-sdk 3.1.417
• dotnetfx 4.8.0.20190930
• git 2.35.1.2
• git-fork 1.71.0
• git.install 2.35.1.2
• github-desktop 2.9.12
• gittfs 0.32.0
• hxd 2.4.0.0
• KB2533623 2.0.0
• KB2919355 1.0.20160915
• KB2919442 1.0.20160915
• KB2999226 1.0.20181019
• KB3033929 1.0.5
• KB3035131 1.0.3
• KB3063858 1.0.0
• KB3118401 1.0.5
• microsoft-windows-terminal 1.12.10732.0
• netfx-4.7.2 4.7.2.0
• notepadplusplus 8.3.3
• notepadplusplus.install 8.3.3
• nuget.commandline 6.1.0
• powershell-core 7.2.2
• pwsh 7.2.2
• resharper-platform 213.0.20220322.123209
• sql-server-management-studio 15.0.18410.0
• sysinternals 2022.2.16
• totalcommander 10.0.0.20210903
• vcredist140 14.31.31103.20220402
• vcredist2015 14.0.24215.20170201
• visualstudio-installer 2.0.2
• visualstudio2019enterprise 16.11.11.0
• vscode 1.66.0
• vscode.install 1.66.0
• windirstat 1.1.2.20161210
• wireshark 3.6.3

But, yes, that is a lot of packages, and just thinking about running regular updates is a headache. If these were installed manually, I’d have to go off to each vendor’s website and get updates manually. Luckily, and really the entire point of this, Chocolatey has a very cool feature which I call “upgrade y’all,” where you tell it to upgrade any outdated packages (from an elevated command prompt):

choco upgrade -y all

If I wanted to back up this configuration and deploy it to another machine, I would need to drop the list into a text file somehow, and once Chocolatey is installed on the new machine, tell it to install the things from the text file. Fortunately, Erik Hougaard has written a nifty script to do that for you, leveraging the amazing PowerShell.

Side note: if you want to know the best way to administer SQL Server, check out dbatools.io, a collection of hundreds of free PowerShell commandlets that make your life as a data professional easy, from database migrations to setting up availability groups.

Share your favourite Chocolatey recipes in the comments below and let us know how you jump-start your installs.

Bonus round

• Check out Boxstarter for automated Chocolatey-based Windows installs.
• You may not have heard of WinGet (styled winget), which is a similar package manager for Windows 11. Jérémie Bertrand has a great article on switching from Chocolatey to WinGet if you’re interested.

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