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Windows 2012 R2 server not installing updates

I've in inherited a Windows 2012 R2 that doesn't look like it every been updated - I've run manuel updates and there are a few there but i've not installed them yet I thought I would try to install 2018-07 Security Monthly Quality Rollup for Windows Server 2012 R2 for x64-based Systems (KB4338815) - But I get an error message reading not applicable to this computer.

I am installing the right update it's a R2 update going onto an R2 Machine and it's getting the updates from the internet

Any ideas?

Or is there a better strategy?

First you need to install https://www.microsoft.com/en-us/download/details.aspx?id=42334 which is q requirement for all future updates. Then it will work.

ASKER

Thank you download and run clearcompressionflag.exe first then KB2919355 but still getting this update is applicable to your computer
I've also download and run KB2919442 is a prerequisite for KB2919355

When I run clearcompressionflag.exe it doesn't seem to do anything?

Any advice?

I never had problems following the installation instructions which are: "These KB's must be installed in the following order: clearcompressionflag.exe, KB2919355, KB2932046, KB2959977, KB2937592, KB2938439, and KB2934018.
KB2919442 is a prerequisite for Windows Server 2012 R2 Update and should be installed before attempting to install KB2919355".

Clearcomp. Does not show output, that's normal.

ASKER

Yep that what I followed but KB2919355 will not install

Check if that update is already installed on the PowerShell. Launch:

get-hotfix | sls 2919355

Open in new window

If it returns no outpit, it is not installed, yet. Else, it is already installed.

ASKER

Run the command it's not installed

So KB2919355 return "not applicable" on your machine? Just to make sure, since you wrote "applicable" before.

ASKER

Yep sorry KB2919355 not applicable

Strange. I would now take the windows setup and do an in place upgrade and afterwards retry to install KB2919355.

Or is there a better strategy?

WSUS. It will tell you what you're missing, what is required, what has been or has not been superseded, etc. Its free so there's not really any excuse to use it to at least catalogue your environments patching levels even if you don't use it for patching.

One should use wsus, yes, but it does not help you to avoid detection problems like this one which are based at the client side.

Ian, did you ever do an in place upgrade? It's described here https://www.tenforums.com/tutorials/16397-repair-install-windows-10-place-upgrade.html (same with server 2012 R2).

Did you try the older updates first, just to see what would happen? Might be able to identify some patterns.

ASKER

Yep some especially the feature pack will install
I and wondering if there something else that has to go on first?

No, nothing. I took a clean 2012 R2 and went straight to Update 1 (KB2919355) and could afterwards install the newest updates without any problems. Use the inplace upgrade process.

ASKER

Hmm ok It won't take 55 - I wonder what's next

You did the inplace upgrade already and followed the prerequisite steps to install KB2919355, but still "not applicable"?

ASKER

Yep I ran the exe file and the KB55

But it didn't work

Ian

I cannot quite believe that. Please offer the output of the PowerShell command

Get-hotfix

ASKER

User generated image

User generated image

Sorry, did you do the inplace upgrade? It does not seem so, since after the inplace upgrade, no updates would show as being installed at all. Do the inplace upgrade.

ASKER

Right sorry no I missed you comment and link about inplace upgrade = i'll try that first.

ASKER

McKnife - I am little confused with 2012 R2 where do I run the inplace upgrade from? Do I make an ISO of the original installation media?

Also this server has SQL 2012 installed and one application that sits on top of that will these be preserved?

Ian.

Applications will be preserved as well as their settings.
You start setup from the original 2012 R2 setup media and continue the process as shown in my link.

ASKER

Ok thank you I'll try it

Ian.

ASKER

I try the in place upgrade - I create a ISO and run setup from within the windows server itself, but I got a message saying I couldn't upgrade I could only do a fresh install which isn't going to work for me.

I've also tried WSUS Offline and that didn't work either

Any other ideas?

Ian

"message saying I couldn't upgrade I could only do a fresh install" - that would be expected behavior if any of the following were true:

your downloaded either is either of another language or it is another edition (datacenter, for example), or it is not 2012 R2, but 2012.
Please verify that.

ASKER

Hmm it was the evaluation iso in English and I told it to install the standard edition - I'll try again with original media.

Also can I upgrade it straight to 2016? I have a spare copy of that laying around

Ian

You cannot use the evaluation media for this, it needs to be the retail or VL media, just the thing that you installed with, back then.

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ASKER

I see thank you for all your help - I'll give it a go.

I wouldn't recommend upgrading to 2016, as you already have enough stuff going on. If you wanted to set up another server in place of this one, that's fine.

ASKER

Although not totally resolved I’ve been point in the right direction.

You don't need to close the question before you try.
And I agree with masnrock, you don't upgrade simply because you can. You should not rush this, maybe plan a little and stick to 2012 R2 until planning is finished.

ASKER

Ok thank you

ASKER

I just wanted to update the thread and say after doing the in place upgrade recommended by McKnife, I was able to install updates including KB2919355

Thanks Again for being so patience

Ian

Thanks for sharing. Many askers here simply forget to share the final result - appreciated.