Preparing for Large Batch of Windows Server Updates going back to Aug 2013

How often do updates to Windows servers interfere with a servers performance, services, and/or software?
In other words, after installing updates, what level of validation should be involved in making sure the updates are not causing issues on the server? With such a large batch of updates to install this weekend, I want to be prepared for worst case scenarios
involving systems not booting up, required services not starting, software conflicts, etc. We have a 2008R2 server and a 2003 server to test on, but they're not really representative of the production servers in terms of the roles they play and services they
run. Just to clarify, this is my first time updating Windows servers.

1. There is a long term mantra: Test updates in test environment before applying updates in production systems.
2. Situation is complicated a bit by the fact that there are "direct"  and WSUS update packages.
3. MS states that updates are tested thoroughly. I do believe they do a good job.
4. I work with Windows for a very long period and I am pretty sure that the quality of software including updates is increasing.
5. I understand your hesitation, my first updates caused the same tension.
6. You have a possibility to download updates for "direct" application from catalog update repository. Problem is that you do not know the optimal order of installation. Fortunately information on problems and their solution comes fast from Internet if you
listen on right channels.
7. From my point of view the danger stems from some optional updates, namely drivers may send your server to unexpected operation. I do prefer drivers and firmware from server/computer vendor, though some irregularities exists.
HTH
Milos

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