It’s All About The Choco(latey?)

Things chocolate is good for:

  • eating chocolate – the darker the better
  • chocolate fondue
  • chocolate brownies
  • triple choco cookies
  • installing software

> installing software . . .¬†(WAIT WHAT ?!?!?!)

The last one isn’ quite right – but, no matter how sweet chocolate is, chocolatey might be even more delicious!

Ok, clarification: Chocolatey (short: “choco”) is a package manger for Windows that actually works really well, has loads of packages in the public repo – and you can create packages yourself pretty easily!

– if you are not hyped right now – you may as well leave ūüôā –


In 2011, RealDimensions Software LLC. (you may as well say “Rob Reynolds”) started developing a package manager based on NuGet. In November 2016,¬†Chocolatey Software, Inc.¬†was formed as as spinoff of RealDimensions Software. Currently, the community repository of Chocolatey features more than 4500 packages, receiving approx. 1 download/second!

Chocolatey comes in four different flavors: “open source”, “Pro”, “MSP”, “Business” – not judgding, Rob should have called them “Vanilla”, “Choco Chip”, “Choco Muffin” and “Triple-Choco-Chip-Explosion”. (see¬†

Not going to tell you which version is best for you – just saying the free OSS version is sufficient for most of everyone’s daily¬†activities concerning installing and updating software, the business (‘biz’) edition rocks your workplace! (more on this later on…)

You can use Chocolatey as you’d use any other¬†“classic” package manager on a Linux system – by typing

> choco search firefox
> choco install firefox
> choco upgrade firefox
> choco upgrade all

in your command prompt.

If you’re not keen on using a terminal,¬†you can use the, still-in-progress – but ready-for-everyday-usage ChocolateyGUI. (Version 0.15 is soon to be release, and there¬†will be some HUGE improvements over the 0.13.x version!)



Pretty straight forward: follow the instructions on

> iwr -UseBasicParsing | iex


Why would I use it?

Using a very old and bad analogy: time is money, money is time, choco saves you time, so choco saves you money!

Using Chocolatey at work (yup, I’ve been the one that has¬†been assigned with setting up¬†a Chocolatey¬†environment :-)) – I soon started to realize that¬†keeping¬†packages up-to-date is a never-ending time-consuming task. Being a software dev, I soon wanted to automate the process of pulling in packages from the community repo and putting them onto our internal server. (most companies won’t be happy with directly accessing¬†executables from a¬†public feed – you’ll want to have them at a secure location and be virus and malware-checked on a regular basis. ProTip: use ProGet for hosting a Chocolatey server. (Free and Commercial options available!))

Asking around on how to best implement such a feature, I came across the gitter-channel of Chocolatey.¬†Fun fact: due to the time zones the choco-devs are living in there’s basically always one of the core-devs available for Q/A!

If you get the biz license, there’s a feature called ‘internalizing’ which downloads and recompiles a package so you can put it onto an internal server straight away! – Create a Jenkins job with a little PowerShell magic behind¬†it and BOOM: time saved!

So now, I just enter the name of a package I want to internalize and hit enter. The downloaded package(s – yes dependencies included) will be virus checked, binaries put on a local unc-share and the recompiled nupkg put onto the local Chocolatey server.

Checking ProGet, we currently have 338 packages with more than 3000 downloads on our server that I set up in December, what a hassle Рand how time-consuming Рthis would have been without the internalize feature!

This is how a Jenkins job (the PowerShell “magic”) could look like for such a “internalize job”:

$package = $env:PACKAGE_ID
$targetserver = $env:INTERNAL_SERVER
$uncshare = $env:INTERNAL_UNC_SHARE

choco download --recompile $pkg --resources-location="$uncshare\$pkg" -source="$sourceStream" --force
$genpkg = ((gci *.nupkg -recurse).FullName | Select-String -Pattern $pkg)
choco push $genpkg -source="$targetserver" -api-key="$apikey" -Verbose -Force


Matt Wrock was kind enough to give us Boxstarter. It adds the missing pieces to Chocolatey!
You want to install software with choco? – no prob.
You want to¬†set-up a dev machine or a buildserver, installing dozens of packages in a row, automatically restarting the machine whenever necessary and continue installing afterwards? – that’s where Boxstarter fits in!
You want to install all available Windows updates, add tray icons¬†after installing choco packages, change windows explorer options, in other words: customize a windows environment? – that’s where Boxstarter fits in!
An example Boxstarter use to set various Windows options, install Firefox, Visual Studio Community, Visual Studio Code, NotepadPlusPlus and also install security relevant Windows updates:

# Boxstarter options
$Boxstarter.RebootOk=$true # Allow reboots?
$Boxstarter.NoPassword=$false # Is this a machine with no login password?
$Boxstarter.AutoLogin=$true # Save my password securely and auto-login after a reboot

Update-ExecutionPolicy RemoteSigned
Set-WindowsExplorerOptions -EnableShowHiddenFilesFoldersDrives -EnableShowProtectedOSFiles -EnableShowFileExtensions
Enable-PSRemoting -Force

choco install firefox -y
choco install visualstudiocommunity2013 -y
choco install VisualStudioCode -y
choco install notepadplusplus -y



Just for your notice: Chocolatey can be¬†build and run with mono.¬†I’m still fiddling with PowerShell on Linux to get everything working as I’d like it to – but¬†there is no¬†reason it _cannot_ work, and I’ll put up another post as soon as I’ve got some working samples to put on GitHub ūüôā


Future Outline

Currently I’m focusing a lot on Chocolatey and trying to find¬†the perfect place for this tool – both – at work (Windows) as well as at home (Linux). I’ve just started to grasp what this tool is able to do and may be able to do in the future, so I hope more posts with how-to’s, scripts and small tools (GitHub), and my experience (and experiments! :-)) will show up on¬†this blog!

For now, I’ve started to put up some scripts I use:¬† – they basically work but need some extra maintenance.



2 thoughts on “It’s All About The Choco(latey?)

  1. We have built a service on top of Chocolatey to manage applications on multiple computers in multiple domains/organizations, through a single website. We made it for ourselves to deploy applications on our customer’s computers, but now we are sharing it for free. Take a look at

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