Month: June 2017

Using Chocolatey In Corporate Environments (Part #1)

It’s been about a year now that I’ve started pulling in Chocolatey as a tool for software deployment for the development teams at my workplace.
As of today, the setup of development machines, buildservers as well as specific terminal-hosts have been fully transformed from manually following many-pages of wiki install instructions to a single ‘meta-package’ that takes the hosts from 0 to 100 in ‘no-time’ (really, just like an hour compared to a full work-day previously!). And yes, all machines receive their very-own configuration, licensing for different software packages etc. etc. hyped? so am I!

Even though this is pretty obvious, it doesn’t hurt to recollect:
Having the install-procedure as well as the configuration in code (PowerShell in this case) makes it repeatable and less error prone! In addition to that, you’ll want to put your code under version control, so you’ve got the history covered!

Package Separation

For the sake of convenience I’ve decided to split up the packages that actually install software and the configuration of this software into separate packages.


Internalize Everything!

In a business scenario, you probably don’t want to rely on public package source repositories (for multiple reasons) – so downloading the wanted packages, doing a virus-check and putting the artifacts on an internal-only server is basically what you want 99% of the time.
This can be a challenging task when done manually, trust me – I’ve been doing this and trying to automate it for about a month, but wait – this task already IS fully automated via the ‘internalize’ feature!
This feature is only available in the ‘business’ licensing model of Chocolatey, if you’re planning on using Chocolatey for work – go get a trial and let the magic work for you!

It is literally as easy as this:

choco download --internalize $pkg --source=https://repo...
choco push $pkg*.nupkg --source=https://myorg-choco... --api-key=$apikey

If you’re keen on going a step further, I’ve put up some sample ‘internalize’ script that I use to fetch packages via Jenkins CI. [internalize.ps1 on GitHub]

Completely Offline Chocolatey Installation

.\corporate_install.ps1 -dont -bug -me -with -external -resources

If you want to get into a lot of detail here, go check out the manual at

One thing that is currently missing (afaik) is a completely-offline Chocolatey installer.
You can always take the install.ps1 from and modify it to your needs – but when you look at chocolateysetup.psm1 you’ll see that even a offline copy of chocolatey.nupkg could try to download a .Net Framework from a Microsoft mirror.

To overcome this rather annoying circumstance, I’ve decided to modify the base install.ps1 a little further to install a .Net Framework, if missing before installing Chocolatey – so no public internet connection is needed at any point.
I’ve put my efforts down into a script called corporate_install.ps1.
The script can be parametrized, so you should be able to fit it into your organization by just passing the right parameters!

You’ll also notice I’ve pulled Boxstarter, a great project adding reboot-resiliency (among many other cool features), into my base setup – this is because I use it all the time!

MIND! The first thing you’ll want to do when using chocolatey in a corporate environment is to remove the public community repository. (this is automatically done in my ‘corporate_install.ps1’ ;-))

choco source remove --name chocolatey

Artifact Server

Currently I’m using ProGet as artifact server, for solely two reasons:
1. It’s extremely easy to set-up and use
2. It’s got a feature called ‘package cache’

The package-cache feature pulls the wanted package from the HQ to the local package cache when first requested.
With this feature we set-up ‘location-based’ servers for our remote-offices. Now all employees are pulling packages from their ‘closest’ server – so no extra bandwith to HQ is needed.

Configuration Deployment & Software Licensing

This is probably the most ‘tricky’ bit from the currently existing setup and therefore will get an extra blogpost asap. Just note: we’ve created a simple ‘configuration service’ containing information about ‘software’ and ‘licensees’ (‘software’ matches the package-id and a ‘licensee’ currently is either a hostname or Domain\Username). This information can be pulled from the chocolatey*.ps1 scripts via inline C# … … …

Multiple Chocolatey Package Source Repositories

If something turns out to be working great, you’ll want it to scale with your needs. In order to be able to scale ‘company-wide’ it seemed to be a good idea to split-up our Chocolatey packages into multiple package repositories for the following reasons:

  • packages could be grouped logically
  • (office packages, developer packages, testing packages, …)

  • package visibility could be controlled by the activated package source repositories
  • (office hosts don’t even get the chance to install i.e. 20GB of VisualStudio)

  • favor package versions based on different feed-priorities for different teams/ user groups
  • (team ‘X’ is on a ‘slow’-feed that only contains VS2015 update I, not II because a certain VC compiler settings would be unwanted for Product X, team ‘Y’ is on a ‘fast’-feed with all the VisualStudio versions available)

We’ve came up with a ‘hierarchy’ that can be described as follows:


I will devote a whole blogpost to this, so stay tuned 🙂

Chocolatey Support

What should I say? I’ve had a couple of talks with Rob Reynolds, Gary Evan Park, Rich, Kim, Pascal,… (yup, basically the whole Chocolatey team). If you need help or have any question – just get in contact via gitter, they’ll be happy to help.
I will also be hanging around there sometimes 😉