Server 2012 R2 Essentail - Windows Updates

Question

Afternoon all, I have recently taken over a site with a 2012R2 Essentials server which has been unpatched since 2015. (updates was set to notify and not download) In trying to upgrade a specific piece of software related to the real estate industry running on the server, I encountered an error and had to roll back the upgrade which worked fine. In order to get support from the software vendor I have to apply all Windows updates, and bring the server up to date.

I have never had to work on a server that is this unpatched, what is the best way to go about this? Windows updates do show 93 available updates but would appear to only show updates to early 2017. What's the best approach to take here to bring this server up to date correctly as to not cause issues on reboot, potentially causing bigger issues. There is Shadow Protect in place (which is great), but I would rather not be in the positing of having to restore because of the update process being done incorrectly. I would really appreciate some feedback on the best way to approach updating this server before I commence.

Answer 1

If your installation media was a gold or RTM version then you'll need to install this set as a prerequisite. When 2012 R2 RTM'd the updates were called rollups and were not cumulative and they also had to be installed sequentially in correct order.
https://www.microsoft.com/en-us/download/details.aspx?id=42153
https://www.microsoft.com/en-us/download/details.aspx?id=42334

then at this point; or if you installed Windows Server 2012 R2 with Update then you can start using the cumulative updates here.
the latest SSU
https://www.catalog.update.microsoft.com/Search.aspx?q=KB4566425

followed by the latest Monthly Rollup
The latest always contains new fixes plus the previous monthly update.
https://support.microsoft.com/en-us/help/4009470/windows-8-1-windows-server-2012-r2-update-history

--please don't forget to Accept as answer if the reply is helpful--

Answer 2

Hi,

You can use "check for updates" to upgrade your windows to the latest version. This should be the easiest way.
https://learn.microsoft.com/en-us/troubleshoot/windows-client/deployment/get-updates-through-windows-update#detailed-steps-for-windows-server-2012-r2

But if you would like to manually install the KB, please first understand the types of updates.
https://learn.microsoft.com/en-us/troubleshoot/windows-client/deployment/standard-terminology-software-updates

DSPatrick has provided a good guidance for you to manually update the windows.

1. Below is the update history for Windows server 2012 R2. All the security-only updates in the list should be installed sequentially in correct order
   https://support.microsoft.com/en-us/help/4009470
2. For Monthly Rollup, only the latest one needs to be installed. All previous fixes have been included in the latest one.
3. Before you can install the latest monthly rollup, you will need to first install the latest SSU KB4566425
   https://support.microsoft.com/en-us/help/4566425/servicing-stack-update-for-windows-8-1-rt-8-1-and-server-2012-r2

Hope the information helps.

Thanks,
Eleven

----------

If the Answer is helpful, please click "Accept Answer" and upvote it. Thanks.