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I am primarily a Linux guy but from time to time have to use Mac or Windows for whatever reason. On Linux, keeping the entire system up to date with the latest software releases is usually the work of one simple command. Likewise installing something new is as simple as naming the package you want. There is never any fumbling with downloads or assorted crazy installers.

Homebrew has stepped in to fill the missing roll on Mac OS X, with homebrew cask taking care of installing and updating binary distributed software where Homebrew alone takes care of anything that is distributed as source.

I am, however, still high and dry on Windows. Ninite is a great stop gap and usually the first thing I do (after however many rounds of Windows updates it takes) but the software selection is limited to a handful. A useful handful, but by no means all the things I need on a Windows system.

Is there some installer that can ease the pain of installing and managing assorted portfolios of Windows based software?

Note also I am not in an enterprise environment and am not looking for a network deployment tool. Cygwin (although indespensible) is not what I'm looking for here either.

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I'm a fan of chocolatey for that - its a front end for nuget, has a fairly wide range of packages. It has a command line interface and ties into a lot of standard windows tools. It also ties in with things like cygwin and python. It has roughly 1700 packages including flash and notepad++.

I don't think it picks up existing software automatically (If you use it, its probably easier to use it from the start ala ninite, so that you can take advantage of its one line update option!), so I'd use it alongside something like securia psi on an existing system to tell you what's been updated.

It also lets you create a list of packages in the form of a xml file to download - you can even explicitly set the version as well.

EDIT: I just noticed the upcoming, official oneget tool uses the same repositories initially. I naturally cannot recommend a bit of software thats vaporware as a solution, but this kind of shows the sort of traction chocolatey has.

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I recommend Chocolatey. Once you have installed the software you want using choco install firefox, for example, you can run one simple command:

choco upgrade all

to check for and install all available updates for all the apps you have installed / registered with Chocolatey.

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As you have discovered, there isn't really anything in Windows that covers it all, so you might have to use several in combination (and still not be guaranteed full coverage).

For years, I have used File Hippo and am happy enough with it. I use it in conjunction with Sumo, so you might want to look at both.

Alas, neither site gives a list of the supported applications, but I know from experience that they detect dozens, if not hundreds on my laptop, and it is not all mainstream stuff.

There are further recommendations at Gizmo's TechSupport Alert. I can recommend the site as great source of reviewed & rated freeware, although I have not read that actual page.

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