Automating Windows Series – Why Chef

Posted: November 10, 2015 in Automation, Chef
Tags: , , ,

This is part of a series of posts on automating Windows and deploying systems in the real world of enterprise operations. I’ve focused the series on the those nuances and problems that I’ve hit trying to deploy the various software stacks found in a typical Windows centric enterprise company.

The first question is why I chose Chef, especially considering it’s roots are definitely not in the Windows space!

Ultimately a choice had to be made and at the time it was made because of the following points.

  • A large and vibrant community (Helped by the fact that Steve Murawski, an ardent fan and early DSC adopter, joined the Chef team).
  • Chef identified early that it needed to embrace Windows and demonstrated a clear path to incorporating DSC into it’s DSL.
  • Templates! Oh how templates makes deploying configuration files, where one or two settings need to be dynamic, so simple. I can’t highlight this enough, being able to drop text files and then dynamically modify a single field based on environment or node specific variables is a godsend.
  • All the core functionality is open source and provides a complete system for managing and deploying configurations.
  • The Chef server and in built search tools give operations the ability to do some simple but dynamic service discovery and configuration. Not as good as doing service discovery native within the applications but better than static configuration files.

Of course the big question is why not straight Powershell DSC? I spent a fair bit of time with DSC before I adopted Chef and I found there were some fairly large hurdles to overcome. Some of them are still relevant today and some have been remediated or will be in the not to distant future.

The really painful problem relates back to managing text based configuration files which have some dynamic content within them. There’s no native functionality within DSC that will allow you to handle config files in the same manner as say Chef, so you have to implement your own logic. I went right down a rabbit hole writing a custom DSC resource to manage nodes in a XML file for one POC before I realised I was going to have to do something similar for every text based file format.

There’s a basic framework around DSC configuration deployment that requires you to write a lot of Powershell to assemble a deployment system from base DSC to deployed configuration. It can be done but it takes a lot of work to maintain that sort of system and I’d rather spend my time writing configurations than the plumbing to keep deployments working. DSC being primarily a DSL means you can use it different deployment and configuration scenarios but ultimately it’s not a singular tool for the end user. Microsoft and others (like Chef) are going to wrap their own deployment methodologies around the DSC DSL.

So Chef got chosen as the platform for attempting to automate the Windows beast. Stay tuned for the follow up articles where I discover it isn’t all roses in the automation world.

To get started with Chef hit the root of their official documentation at or for a guided set of tutorials


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