How do I make sure that Windows is up-to-date?

Summary: You can make sure that Windows is up-to-date by either enabling Automatic Updates or by visiting the Windows Update web site.

How do I make sure that Windows is up-to-date?

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It seems like every week there's news about some newly discovered vulnerability or bug fix in Windows. And of course the stories tell us that we should all rush out and install the fixes immediately or the world will come to and end.
Or something like that.
In fact, Microsoft does announce updates weekly. With that rapid a rate, how should you stay on top of things and make sure that your system is up to date?
There are several options.

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Microsoft provides a service that runs on your machine and - on terms you control - automatically checks for Windows updates. Once found, it can then download and install them for you.
The specific labels vary slight across Windows versions, but to configure automatic update click on Windows Update in the Windows Control Panel.
In Windows 7, this is the Windows Update options dialog:

You have four basic options controlling how Automatic Update works:

• Never check for updates - as you might expect this basically turns the Automatic Update feature off.
• Check for updates but let me choose whether to download and install them - with this setting, Windows Update will only check the Microsoft site for updates, and if there are any that apply to your machine, it will alert you, and nothing more. You can then choose to download and install, or not.
• Download updates but let me choose whether to install them - with this approach, Windows Update will check the Microsoft site for updates and actually download any that apply. Once downloaded, you're notified that they're available and can initiate the install at your convenience.
• Install updates automatically - finally, you can just have Windows Update do it all, on a schedule you can define. Check, download, and install as soon as updates are available. (Note that depending on the updates you receive, your machine may be rebooted as part of this process.)

In Windows 7 you can also control whether or not the process should include both important and recommended updates, or just important. (You can still receive important and other updates by visiting the Windows Update web site, which I'll discuss below.)
Windows 7 also allows you to specify that all users can install system updates via Windows Update, and wether or not Windows Update should also update other Microsoft software on your machine (aka "Microsoft Update" as opposed to just "Windows Update").
For what it's worth, I like to know what's happening to my machine(s) before it happens so I typically select the "Download, but let me choose" option.
Many people find the concept of Automatic Updates a little too spooky or intrusive. Others just want to have even more control over exactly what happens when. And of course there are folks who are using older versions of Windows.
For all these people there's the Windows Update web site.
The first time you visit Windows Update, it'll download a component onto your machine that handles the inspection of your current Windows versions. That list is then compared against the latest releases and you'll informed of the differences. You can then select which components to install.