How to catch up with 4 years worth of service packs, hotfixes, patches

Home Forums Server Operating Systems Windows Server 2008 / 2008 R2 How to catch up with 4 years worth of service packs, hotfixes, patches

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    I have recently started working in a small business where the systems/server administrator did not keep up to date with server patching. There are 2 servers: 1 Windows 2008 and 1 2012. I have been tasked to update the servers with patches current to January 2018. A few questions:
    – Will MBSA work on these servers?
    – There are roughly 400 patches, 68 of which are critical updates.
    – Can WSUS be used for only 2 servers or is Windows Update enough?
    – There is a rollback feature built in to Windows Update if I recall.

    Overall, what is the best way to proceed here? Do the patches have to be applied in reverse order and how to determine which are absolutely essential From the MSDN documentation I have read, it’s obvious to make a back up of these servers before proceeding. Both servers host several VMs for the company.

    Is there a document, site or external resources where I could find some specific direction on the questions above? Did a lot of searching but no specific guidance on how to proceed restoring/applying patches on servers that are several years behind.

    Thank you in advance.

    Peter Brabson

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