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Windows updates on server 2008


I am planning to reboot a few servers at different time (during mid-night) but windows security updates(about 20 updates are from last year) have not been applied to them.

Should I run them all together or just only updates that have been successfully applied to other servers.

I had some issues with windows updates that OS did not work after windows updates so I had to remove the installed updates in order to fix the problems.

What would you guys do?

One server is running 2008 SP2 with Exchange Server 2007, I would not want this go down next morning due to the windows updates failure or cashes.

Microsoft Legacy OSMicrosoft Server OS

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Lionel MM

8/22/2022 - Mon
Lionel MM

Without knowing which updates and what problems it caused this is difficult to answer. There may have been other items on the other server that is not on this one--as a general rule I would apply all the updates but if I know of specific updates that cause problem in my environment then I would uncheck them and not install them. Are these virtual or physical servers? If virtual simply make a snapshot before doing the updates so you can go back if issues occur.

Thank you for your anwser. It's physical server. What would be the quickest way to restore server if the system does not come back after windows updates fail?
Lionel MM

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