Should "Windows Update" run automatically on a production server?

Question

I have a web server running OS "Windows 2008 R2 - 64 bit" that hosts several websites for my clients (small companies). Since June 2013 "Windows Update" automatic updates has been turned off. I was told to turn automatic updates off as it can cause the server to crash, which would obviously affect my clients.

My concern is obviously that when I ran Windows Update today I see there are 130 important updates, most of which start with "Security Update...", others just start "Update...".

What is the best practice regarding Windows Update, and particularly turning on Automatic Updates, for a production web server?

The web server runs IIS 7 with SQL Server 2008 R2. The sites are all ASP.NET sites, some Web Forms, some Mvc.

Hopefully this isn't too generic a question. I'm obviously afraid that I might have to install these updates and risk bringing the server down.

Answer 1

Probably better asked on serverfault

Start with this question over there:

To update or not to update

https://serverfault.com/questions/134324/to-update-or-to-not-update