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Chocolatey and Chef aren't rivalrous. When I've managed Windows/Linux mixed environments before, I did use Chef, and I used Chef to install Chocolatey packages.

Chef isn't just CM, it's also a lot of policy enforcement tooling these days. I don't have much use for it anymore but it does have its niche.

Chocolatey is a proxy-package manager, automates fetching packages off the Internet installing them (often through the packages own .msi or other installer). So it doesn't compete against Chef any more than yum or apt-get or Homebrew competes with Chef. Chef supports Chocolatey directly.

That being said, the experience on Windows is abysmal. The implementation with ruby on Windows is sloooooooow. You wait seconds just to get things like version.

Agreed. Which is why I find it odd that their products are in a mismatch of verticals. This strategy only makes sense if more acquisitions are on the way.

Perhaps they are looking at Habitat which is a cross-platform package manager that competes with Chocolatey somewhat.