Windows Update has never been turned on so................

I am working for a client and found out that they have never had Windows Updates turned on for the Windows Server 2008 and SQl Server 2008 web server.

There are 127 updates since 2011 and also SP2 has never been run for the SQL Server 2008 R2.

So I do realize that trying to run them all at once is high risk. And I won't be doing that.

Are there any secrets to the best method of running them? Do I look at the dates and run them by dates? Or how do I assure I'm getting them in the right order?

(If they were run all at once, would MS get them in the right order?)

I have run them all at once on systems where there are over 100 and that was bad news which I don't want to revisit.

Plus there are a lot of things that they say they update that I don't even know what those things are. Should I just ignore those?
ie: Best Practices Analyzer for....

And there are 3.5.1 framework updates. And I am not using 3.5 I am using 4.5. Should I run the 3.5 updates or skip those?

There are updates for IE10 and IE11, and this machine has IE8. So?

Starr DuskkASP.NET VB.NET DeveloperAsked:
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Joe JenkinsConnect With a Mentor Commented:
I typically will install service packs first.  Then the highest IE and then only the frameworks that I use in my environment.  Doing that will eliminate a lot of those updates.  

As for 3.5.1, a lot of software out there uses 3.5.1 so it's possible that at least one piece of software on your machine is using that framework and thus it will need to be installed and updated.

The longest part of your entire update process will be the .NET framework installations/updates.  They take entirely too long in my opinion but it has always been that way.
I typically will install service packs first.

This is a good plan since "usually" service packs include previous interim updates. That should eliminate a lot of them.
Joe JenkinsCommented:
Correct, they "wrap-up" those smaller ones.  Installing one service pack could wipe out may of those updates.
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Anthony PerkinsCommented:
As to the SQL Server Service Packs, what specific problem are you trying to fix?  If it is just so that you can have a warm feeling that all is well in the world, think again.
Starr DuskkASP.NET VB.NET DeveloperAuthor Commented:
Wow. That's useful. Let's pose a feeling of dread but don't back it up with anything.

I always install service packs for a warm feeling that all is well in the world. Isn't that why Microsoft releases them?
Anthony PerkinsCommented:
I think you are missing the point and it really depends on your setup.  If you are managing half a dozen servers in different environments, then certainly it is doable to update with the latest Service Pack.  I would however never consider upgrading with the latest CU unless I was trying to address a specific problem,
However, from my experience, I would not recommend this practice in an enterprise with dozens of servers in different environments.  It just makes no sense whatsoever, where you have anything more than a casual testing phase.

P.S.  If you would rather I did not contribute, feel free to say so.  You may not like my answers, however it is my belief that t is not appropriate to encourage bad practices that can easily be confirmed by anyone that has some experience using SQL Server.
Starr DuskkASP.NET VB.NET DeveloperAuthor Commented:
Starr DuskkASP.NET VB.NET DeveloperAuthor Commented:
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