To put it simply, patching your Windows machine every 2nd Tuesday of the month can save yourself a lot of time and grief.
A recent example of this is the conficker.c worm (http://vil.nai.com/vil/content/v_153464.htm), which although has not been widely used for any malicious purposes (http://www.nytimes.com/2009/03/29/technology/29spy.html?_r=2&partner=MOREOVERNEWS&ei=5040) yet.
The conficker worm however is exploiting a previously patched vulnerability (http://www.microsoft.com/technet/security/Bulletin/MS08-067.mspx) that was patched in October of last year. Had this patch been applied universally, this particularly sophisticated worm could have been largely avoided. The same can be said for any number of the nastiest worms that have been around (blaster and others come to mind) in recent memory.
For information regarding how to patch Windows, and to have it automatically update (via automatic updates in the control panel), here is some basic info:
http://update.microsoft.com/microsoftupdate/v6/default.aspx?ln=en-us - Windows update page
http://www.microsoft.com/security/default.mspx - Microsoft Security Central
http://support.microsoft.com/kb/306525 - Setup Automatic Updates (windows xp)
http://www.microsoft.com/windows/downloads/windowsupdate/learn/windowsvista.mspx - Setup Automatic Updates (Windows Vista)
And for all you others (apple/linux), here are some resources:
http://support.apple.com/kb/HT1222 - Apple Security Update Homepage
http://www.reallylinux.com/docs/security.shtml - for linux beginners - patches/updates are usually deployed via apt, yum, Yast or whatever package management your distro uses
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