Now you have a package that hasn't been updated in months.

Users asking the maintainer if the package will ever be updated followed by a reply from a member of the Chocolatey team informing them that most maintainers don’t check the comment section for their packages.

You can see evidence of it in the comment section in the gallery. I install my app using my newly uploaded package and forget about Chocolatey two weeks later. If I go and create a package for an app that I use and submit it to the Chocolatey Gallery I would become the maintainer of the package regardless of my commitment to keep it up-to-date. The first person that submits a package for an application becomes its maintainer. Probably the biggest issue with Chocolatey is its package maintenance workflow or lack thereof. Two years later, I have completely given up.

To my surprise they didn't see how huge this was, but I didn't care. Did we finally get a package manager for Windows, one of the things I always envied about *nix and OS X(Homebrew)? I was really excited I told my co-workers sitting around me about this amazing new tool that would finally make setting up new machines and installing applications as easy as a single command. I remember how excited I got when I first heard about Chocolatey.

Chocolatey package