I recently joined Swiss Life as Software Architect and Developer Community Lead, and of course I got some brand new shiny laptops which had to set up… This time, instead of installing everything manually decided to give it a go to a colleague recommendation - Thanks Andrei! use Chocolatey to perform the installations.
What’s Chocolatey? A Windows-only package/software management solution, enabling version management, dependencies, order of installation and a powerful inventory management, between other features.

I digged in a bit and found another jewel named Boxstarter.
Boxstarter builds on top of Chocolatey & provides a repeteable and really easy way to deploy Windows environment installations using Chocolatey packages, which is also reboot resilient, and enables unnatended installations that need “reboot and continue” for any installation that requires it.

Why?

Well if you are a software engineer like me, you’ll appreciate a predefined installation that you can review, and automate in a completely unnatended way. Also it is repeateable so you can restore it at any moment. In addition, you can evolve it, manage versions over time in a controlled way… and that is priceless.

Of course this does not fit all as we all have different Os and different set of favourite tools (except for HotChocolate) but this pretends to provide enough flexibility so we all can benefit and save time through avoiding unnecesary work, automating the tedious installation and setting-up, and also afterwards not remembering if we installed or not a concrete software, component or plugin or enabled a windows feature…

So, once you have a installation script, you can evolve it over time… and is free of human-errors (except on the choice of applications) Essentially, saving time time, reducing complexity, reducing human interaction through automation - and thus, the risk that this (human interaction) brings of introducing mistakes…

More on this on why Chocolatey and why BoxStarter.

Official websites:

Let’s get it done!

  1. First things first - Install Chocolatey
    • First, you need to install Chocolatey. You can do that by running the scripts found here. After you do that, you can start using Chocolatey to install applications. If you have some trouble you can follow the more detailed instructions here.
    • Once installed, we can check that it works by opening PowerShell and issuing a chocolatey command such as choco install vlc. Note we will need an elevated (aka admin enabled) powershell for this. This “semi-manual” installation will ask us if we wan to install the package, or if we allow to install all the packages, in the case it needs an additional package… this is a bit bothersome, but avoidable adding the -y in our command, so let’s do that again. We type choco install vlc -y.
    • To update we should use the upgrade keyword instead of install one, such as: choco upgrade vlc -y

  2. Install BoxStarter. After Chocolatey we can proceed to install BoxStarter, we can use PowerShell or choco for this as it makes it more simpler. Just type from an administrative commandline: cinst boxstarter (and add the -y if you don’t want to be asked) Note: cinst is short for chocolatey install.

  3. Create the script
    Next we can create the Installation script, it is basically made of PowerShell with some Chocolatey commands.
    We can create it as a single text file or any text based HTTP resource (like a Github Gist)[https://gist.github.com/].
    It should look like:

    Set-WindowsExplorerOptions -EnableShowHiddenFilesFoldersDrives -EnableShowProtectedOSFiles -EnableShowFileExtensions
Enable-RemoteDesktop
    
cinst fiddler4
cinst git
cinst vscode
cinst sublimetext2
    

cinst Microsoft-Hyper-V-All -source windowsFeatures

    In my case, I created the script with the purpose of having a developer box for .NET, azure and web development. For this I installed Visual Studio 2019. And added some of the recommendations from Scott Hanselman “ultimate developer tools” and others blog posts.

    The outcome is located in a GitHub gist I created for this purpose and it looks as follows:

    
Set-ExplorerOptions -showProtectedOSFiles -showFileExtensions
Enable-RemoteDesktop

# Some OS feature setup
cinst Microsoft-Hyper-V-All -source windowsFeatures

# Installing some cool software
cinst visualstudio2019professional --package-parameters "--allWorkloads --includeRecommended --includeOptional --passive --locale en-US"
cinst resharper
cinst vscode
cinst azure-cli
cinst git
cinst github
cinst sql-server-management-studio
cinst 7zip
cinst notepadplusplus
cinst sysinternals
cinst powertoys
cinst notepad2
cinst spotify
cinst adobereader
cinst google-chrome-x64
cinst brave
cinst imageresizerapp
cinst skype
cinst f.lux 
cinst sysinternals
cinst obs-studio

    As a note, I configured all the packages for Visual Studio to be installed, as it is always faster to uninstall than to install, so later on I will uninstall the unneeded packages. As I intended to run this unnatended, it is way easier to uninstall them later on than to install.
    You can customize your script by searching the available packages at the Official Chocolatey package search

  4. Run the script
    Once created and reviewed, we can go and execute it from an elevated (read, with Administrator permissions) command prompt. Invoke the the Install-BoxstarterPackage command pointing to the gist created above. For this we will need the RAW link to the GIST script content. In our case it would look like: Install-BoxstarterPackage -PackageName https://gist.githubusercontent.com/joslat/4bc82c9da1d8d5a0054426612944414e/raw/c8456fc0c94a2cb8883fa3d3f5a1abb914d15d54/boxstarter_newdev_script.txt -DisableReboots

    Note that I used the -DisableReboots option as it is stated on the BoxStarter example, but BoxStarter runs from an elevated prompt and can handle reboots and continue with the installation tasks completely unnatended..

  5. And keep it up to date! As mentioned, Chocolatey manages versions and what better than a GUI to help us keep our software base updated. I particularly like ChocolateyGUI. Again, get it with cinst chocolateygui and it will show the installed packages and if they have updates available. And it also allows to export the list of installed packages, providing a valuable help to keep our “list of favorite tools” up to date and in order.

Concluding

A nice recommendation from a now ex-colleague I had the pleasure to work with, turned out to be a valuable addition to my coding weapon array, which I am gladly sharing with you ;) As a last recommendation, if I am motivating you to start using Chocolatey and/or BoxStarter, I’d be curious to see your scripts - if you don’t mind sharing. Or if you were using it already, I am still curious :)

Have fun and enjoy the extra time that these two lovely tools do provide!