I have experienced many woes with Windows Updates.  Including server updates corrupting systems.  This is not a good trend and rolling back the damage done by a failed server update often requires Repair or reinstallation of Windows.  NOT FUN! Remember this before you just click Ok on that windows server update.

Read about some of the more infamous failures below. 20 epic Microsoft Windows Automatic Update meltdowns | Network World.

This illustrates the importance of doing windows updates and keeping an up to date OS (XP is dead!) BUT… Even doing this, some things can still slip through the cracks.  Some for well over a decade!  Read more below. Microsoft fixes security flaw in Windows that existed for 19 years | Hack Read.