It is always a good idea to keep your Windows servers patched with the latest updates (though testing it before hand on a guinea pig is always a good idea to see if a particular patch breaks something).
If your servers are exposed to the Internet, and you do not run Windows updates, it's trouble waiting to happen. I know having a disaster occur tends to be a great motivational factor, but it also means you have to wait for something bad to happen. If you nip it in the bud now, you will save yourself a lot of grief, time, and resources on fixing it later.
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