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Need advice for installing windows updates on our servers

Hi, Im a new Network Admin at my company. One of my new tasks is to get a handle on our servers backup strategy, we have a WSUS server, and when I looked at the update status for our servers, I found that none of them have had any MS updates installed in a very long time. what im looking for is some advice on how/when to install updates to our servers. More or less some best practice advice on how to actually install the updates, and how to choose which updates are needed and which I dont have to install. Im new to this task, so any advice would be great!
thanks in advance.  
let me know if you need additional info.
Windows Server 2003Windows Server 2008Network Operations

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Thank you both for your input. So If im understanding you correctly Soulja, I should not install updates if they dont apply to an issue? Meaning dont just install every update that is available?
im feeling overwhelmed by all of this, we have many servers, and the SUS is reporting many hundreds of needed updates...
dstewartjr, Thank you for the link, im going to be reading that tonight !
Also im new to using this site, if I select a comment as a "solution" does that lock the thread from further discussion? how does that work?
thanks agin for your fast replies!
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Soulja
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If you accept the comment as a solution, it doesn't lock it from further comments.  Yes, you shouldn't just install updates just because they are available. You want to always make sure they don't conflict with custom applications for example. TEST TEST TEST before rolling to production.
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Will use the advice given to put together a plan of action for my server updates. any additional advice is very welcome!
Windows Server 2003
Windows Server 2003

Windows Server 2003 was based on Windows XP and was released in four editions: Web, Standard, Enterprise and Datacenter. It also had derivative versions for clusters, storage and Microsoft’s Small Business Server. Important upgrades included integrating Internet Information Services (IIS), improvements to Active Directory (AD) and Group Policy (GP), and the migration to Automated System Recovery (ASR).

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