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I have my own dedicated servers for running my website, and have been debating the merits of the automatic updates feature in Windows. I am not sure if I trust using it. What if it causes a problem and takes my site offline?
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By far, most of the people we have seen running their own servers, use the automatic updates feature in Windows Server to keep their servers up to date with the latest Service Packs and Hotfixes issued by Microsoft. In the several years this feature has been in wide use, it certainly has proven to be reliable and robust enough to trust in a lights out configuration. Any reports of it causing any additional unintended problems have not proven to be commonplace nor catastrophic.
Our point of view on this topic is this. Which would you rather have? Do you potentially want to run the risk of having a publicly exposed server running with a known security vulnerability that has already been corrected, or take the statistically unlikely chance that an automatic update might have an unintended side effect during installation? If you look at it in this light, we think the answer is pretty obvious. If you are still worried about the possibility of what might happen during the automatic update process, we recommend simply configuring it to take place at a time of day you feel comfortable with in being able to respond to any issues that might arise from its use.
We highly recommend the use of the Automatic Update feature to make sure your servers stay current and up to date with the most recent updates released by Microsoft.
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