Help raise the Chocolatey experiment to the Chocolatey experience and support the Chocolatey Kickstarter! / by Matt Wrock


As described on the homepage of, Chocolatey is like Apt-Get for windows. Now to some, that will immediately paint a clear picture of what Chocolatey is and why it puts the “awesome” into windows just like it does on my winawesomedows system. Others may be asking, “what get?” Or maybe, “that’s ok. I’m not in the market for an apartment right now.” For those who are not familiar with package management systems on other operating systems, Chocolatey makes it easy to find, download and install software. I cant remember the last time I searched for the windows git installer and went through all the screens in the install wizard. I just pop open a command line and type: ‘cinst git’. Curious what you can install via chocolatey? Check out and you’ll find the over 2300 packages available for download and install.

Beyond this immediate value of installation ease, Chocolatey makes it easy to create packages and provides a platform that anyone can leverage to support private and alternate repositories other than the public community feed on

Chocolatey launches a Kickstarter

About a week and a half ago, Rob Reynolds (@ferventcoder) and team launched a kickstarter for chocolatey to help raise funds to not only preserve the value chocolatey currently provides to many many windows users but to help fund some greatly needed enhancements.

Chocolatey costs

While the benefits of chocolatey are free to anyone with access to a windows command line (or powershell console), there is a cost. Hosting these packages entails monthly storage and bandwidth expenses. There is also a huge time investment on the part of Chocolatey contributors and especially Rob Reynolds to address support questions and add features. I’m personally on the chocolatey email groups and I can tell you that I see a constant stream of emails from Rob every day addressing issues, merging PRs, and announcing new features. Gary Park (@gep13) is another individual who immediately comes to mind as an avid supporter. While no one has officially stated this, I can only imagine that asking Rob (husband and father of two) to continue to personally front the recurring costs and invest this amount of time is not sustainable and certainly not scalable.

Professional level offering

In addition to recurring expenses and some first-line support assistance, there are a slew of “professional grade” features the team would like to add to make Chocolatey a more polished experience for those needing to support an enterprise or other business critical infrastructure. These would include, enhanced security, better support for private feeds and other slick features as described in this image from the kickstarter:

New feature: Package moderation

Unrelated to the kickstarter but adding to the evidence that funding can only make things better is a new feature just launched the afternoon prior to this writing – package moderation. One of the most prevelant criticisms of Chocolatey is the fact that it potentially exposes users to malware. This is absolutely true. When you download a chocolatey package, you are downloading software over the open internet and you likely do not know the individual who created the package. The package may state that it installs one thing, but nothing stops it from doing something else or generally doing a sloppy job of installing what it is advertising.

To be clear, I do not believe that this truth implies that chocolatey should not be included in ones tool set. Its not the only package management system with these flaws and there are steps individuals and businesses can take today to protect themselves like pinning to known good package versions or hosting their own chocolatey feed.

Package moderation is one of many other features that stand to enhance the overall security story of Chocolatey. New packages, including package updates must now be approved by a Chocolatey moderator in order to be publicly visible and available to others. Here are some criteria that moderators use to deem a package approved:

  1. Is the package named appropriately? 
  2. Is the title appropriate? 
  3. Does it have all the links? ProjectUrl at the very least. 
  4. Is the description sufficient to explain the software? 
  5. Are the authors pointed to the actual authors and not the package maintainers? 
  6. Does the package look generally safe for consumption? 
  7. Are links in the package to download software using the appropriate location? 
  8. Does the package generally meet the guidelines set forth? 
  9. Does the install and uninstall scripts make sense or are there variables being used that don't work? 
  10. Does the package actually work?

Of course this feature does incur more time on the part of the core chocolatey team and is an example of another area of Chocolatey that this kickstarter aims to support.

Call to action!

So in the spirit of this blog, HurryUpAndWait, I encurage you to hurry up and offer what you feel comfortable contributing and then wait for the success of this kickstrarter! Do you work for a business that uses chocolatey? Perhaps it uses the chocolatey chef cookbook or the chocolatey puppet module. If you have access to those who make financial decisions in these organizations, let them know about how they can help to make chocolatey a more business friendly option that stands to improve its ability to automate.