re: Server 2008 update goes bad...

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It's not a mission critical server, and if it was, I would not touch that shite without having another just like it as a staging server that would get all updates first before doing anything to the production server

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this is one thing that companies fail hard at. And, it is because they are cheap and don't want to pay to duplicate their systems.

Frick, we have over 550 Virtual Servers. We have the ability to snapshot servers prior to doing updates and then failing back if they cause issues. That has been done with maybe 50 machines ever, and probably just maybe 25 of them on a regular basis.

Of course, we also have backups of our stuff and can rebuild them if need be.

The organization really needs to look at their backup solution and figure out why this critical system wasn't backed up. And if it was, why they aren't able to recover it. If it is that critical. They should have regular backups onsite and offsite. And, they should be testing backup recovery on a regular basis.