A lot of folks out there are always wanting to point out that there is Ninite when someone mentions Chocolatey. That is fine, Ninite works but it only has like 90+ things you can install. They are limited by what Ninite can rebundle and redistribute. Both are solid solutions in their own right, but you need to understand the needs and what the two solutions provide to really make a choice on them.

Package Management Approach

Ninite

• Main purpose: Ninite is an installer that keeps off the crapware.
• Keeps everything centralized.
• Has a tight integration with products as the Ninite staff is the only one who updates packages.
• Guarantees success with installs since they control every aspect of the packages.
• Does not take contributions.
• All GUI based unless you pay for Pro version.
• Update apps simply by running the installer again.
• Only use case is for folks who have access to install applications on their machines.
• Only works with software installers.
• Closed source, but free.
• Paid options for CLI.

Chocolatey

• Main purpose: Chocolatey is a global PowerShell execution engine that knows about a packaging format.
• Decentralized with a central community package repository.
• Multiple sources including private sources.
• Packages on https://community.chocolatey.org/packages (the Chocolatey Community Package Repository) are created by the community and reviewed by moderators.
• Packages can embed software, use UNC paths or download software from another location (like the official distribution locations).
• Allows for community contributions.
• Allows for pay for apps to be included as packages.
• CLI focused, although there is a GUI (ChocolateyGUI).
• Easily scriptable which allows for adding setup scripts to things like source control.
• Update apps simply by running cup packagename or choco upgrade all.
• Integration with other package managers (Ruby Gems, Python PIP, WebPI, Windows Features, CygWin, etc).
• Able to be used without needing administrative permissions (portable packages are non-admin).
• Flexible, packages can work with native installers, set configuration, registry, do other tasks or any combination.
• Open source and free.
• Paid options available.

Packaging solution needs (that brought about Chocolatey in the first place)

• Good CLI that is simple to use
• A central repository that takes packages contributions from the community (and is being maintained)
• Ability to use additional/multiple sources
• Meta packages that can chain dependencies
• Virtual packages
• Packages should be easy to create / maintain
• Packages should be concise and be able to be created without worrying about distribution rights
• Unattended installs
• Installation of multiple packages with one command
• Script setup of environments
• A tool that enforces more security automatically

Chocolatey and Ninite : Compare and Contrast

Interfaces:

• Ninite - choose apps from a website, download installer just for those apps. Pay for the pro version and use the command line.
• Chocolatey - open a command line. Install app with choco install packagename <options>. Lather rinse repeat.

Packages:

• Ninite - closed, only items available are what Ninite staff choose to make available.
• Chocolatey - community packages on a central server
• Chocolatey (internal use) - create packages on your own internal repository server

Package sources:

• Ninite - one at Ninite.com
• Chocolatey - central community package repository at https://community.chocolatey.org/packages, create and use public/private sources (folder, network share, OData feed like nuget.org, [community.chocolatey.org] and/or myget.org). See Host Your Own Server for options.
• Chocolatey can also install from alternative sources - choco install bash --source cygwin | choco install gemcutter --source ruby | choco install sphynx --source python | choco install IISExpress --source webpi

Creating packages:

• Ninite - no
• Chocolatey - yes and quite simple. Run choco new test and look at the output - keep in mind that many times it takes complex tasks for managing software installation down to 1 PowerShell function call. Consider windirstat is: Install-ChocolateyPackage 'windirstat' 'exe' '/S' 'https://windirstat.info/wds_current_setup.exe' -Checksum 123456 -ChecksumType 'sha256'
• Chocolatey is building on technologies you may already know:
  • PowerShell - take full advantage of PowerShell.
  • Unattended installations / Silent installation
• Extend Chocolatey easily with PowerShell modules called extension packages.
• Use Package Builder to point Chocolatey to an installer and have it auto-detect and generate a full software deployment.
• Use Package Internalizer to internalize existing community packages quickly.

Available packages:

• Ninite - Handled by Ninite staff, so there's less chance of anything being broken.
• Chocolatey (community repository) - Handled by the community, reviewed by moderators. Possibility of breakages unless using licensed editions of Chocolatey due to CDN Cache.
• Chocolatey (internal repositories) - Handled by you, embedding software or using internal links you control. Zero chance of breakages that you don't control.

Package updates:

• Ninite and Chocolatey community repository both can suffer from keeping packages up to date.
• Chocolatey (internal use) - good to go

Package dependencies:

• Ninite - not really
• Chocolatey - Yes, dependencies are easy! Install Git Extensions, it makes sure Git is also installed.

Versioning/upgrades:

• Ninite - sort of, you just rerun the installer every once in awhile
• Chocolatey - Yes. Consider choco upgrade <pkgname> <options> to upgrade a piece of software. Also consider choco upgrade all/cup all as a Windows Update for all of your 3rd party software.

Conclusion

Chocolatey internal use is the best solution for an organization that has a low tolerance for breakages. There are no issues, you have a secure solution with complete control. You are building on top of technologies you know with a small amount of learning for packaging. Because it is PowerShell, you are not limited to just installers, and you can add additional logic before and after installations, and you are not limited to just "installing" software with packaging.

Ninite is a solid solution if you don't mind not being able to script it and only install the applications that it has listed on the Ninite page. You are, however, possibly guaranteed that you have everything you need to install sheerly by having the Ninite Installer. In that way it may be better than using Chocolatey's community repository, which most packages require access to the internet to download installers that do not have distribution rights with them (Ninite may not incur this extra point of failure, but is quite limited in its offerings). Chocolatey community repository with licensed editions of Chocolatey have almost no chance of breakages due to a CDN Cache of those downloads.

Chocolatey community repository has over 4,000 more packages than Ninite and a community that is driving to continually make it better. If you need to get to older versions of packages, many of the packages on the community repository allow for this. What Chocolatey community repository may lack in the possible guarantee that Ninite provides, it makes up for in features and options. Chocolatey can provide packages for non-free products, have multiple sources and folks can script the installations. Chocolatey is more than just an installer and with that does not require administrative privileges to use.

Both Ninite and Chocolatey community repository solutions suffer from the issue of having the most up-to-date packages available, it's just that Chocolatey is more transparent about it.

When it comes to internal use and creating and hosting your own (or internalizing existing) packages, nothing else holds a candle to Chocolatey. When you step up to Chocolatey for Business, you get access to features that allow an organization to really excel quickly.

Whether you use Chocolatey or Ninite, consider that the two answer the same question differently and that is okay. They can live in harmony with each other and at some point Chocolatey may offer Ninite as package source.