Upgrade Server 2016 Standard > Server 2019 Standard - can't keep files

[Andreas Petzhold]

Hi,

I tried upgrading from Server 2016 Standard to Server 2019 Standard (Desktop) but the installer keeps telling me that I can't keep my files and settings because of a different Edition.

Tried both Standard and Standard Desktop.

dism /online /Get-CurrentEdition says "ServerStandard"

How can I upgrade and keep my files and settings?

Thanks :)

[#2]

How are you trying? To perform an in-place upgrade try running setup.exe from the root of the install media from within windows.

https://docs.microsoft.com/en-us/windows-server/get-started-19/install-upgrade-migrate-19

[#3]

Did you ever get this sorted? I'm also having the same issue - using MSDN versions of Server 2016 and Server 2019.

[#4]

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@BobBuilder1111 wrote:

Did you ever get this sorted? I'm also having the same issue - using MSDN versions of Server 2016 and Server 2019.

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To perform an in-place upgrade try running setup.exe from the root of the install media from within windows.

[#5]

Hi Dave,

That's exactly what I'm attempting to do - under Windows Server 2016 desktop logged in as administrator, open the ISO under Windows Explorer (mounts the image), double-click setup.exe, click through entering MSDN key, eventually get to the screen where in-place upgrade is unavailable - only option is a bare-metal reinstall.

[#6]

So I just now tried using MSDN media (en_windows_server_2019_x64_dvd_4cb967d8.iso) and it works without issue. You probably wouldn't be able to go core -> GUI or vice versa

[#7]

Hi Dave,

Thanks for checking - unfortunately not what I'm experiencing. I'm trying to upgrade GUI -> GUI.

[#8]

May need to investigate what applications and or roles could be blocking an in-place upgrade.

[#9]

Same problem here: Going from 2016 Eval to 2019 Eval (Both Standard Editions, upgrade with or without GUI).

Previous install media delivered via download from a MS Reseller gave me a different error:

"This version is not current" with all 2016 Server patches performed. I am told that upgrading from the Eval is the problem, however the 2016 edition of the upgrade guide explicitly states it was possible to upgrade from an Eval. Purchasing 2016 for the sole purpose of upgrading to 2019 (paid) seems unreasonable.

Anyone have the same issue?

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@Dave Patrick wrote:

May need to investigate what applications and or roles could be blocking an in-place upgrade.

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[#10]

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@mactech wrote:

Same problem here: Going from 2016 Eval to 2019 Eval (Both Standard Editions, upgrade with or without GUI).

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You cannot in-place upgrade to a higher version of windows in any of these scenarios from licensed to evaluation, evaluation to licensed, evaluation to evaluation.

[#11]

So a licensed 2016 install cannot be upgraded to 2019 trial but can be upgraded in-place with a 2019 key?

I seem to remember a downgrade option where a key for a previous version was issued with a new license purchase. Is that a thing or just wishful thinking on my part?

[#12]

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@mactech wrote:
So a licensed 2016 install cannot be upgraded to 2019 trial but can be upgraded in-place with a 2019 key?

You can upgrade Server 2016 to Server 2019 but you will need to use retail or volume media. Evaluation media cannot be used in this scenario. 

[#13]

did you get it fix? im having same issue?@Andreas Petzhold 

[#14]

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@LaythServpro wrote:

 im having same issue?

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What issue are you having?

[#15]

I can't keep files  @Dave Patrick 

[#16]

A wild guess but this one may apply.

https://support.microsoft.com/en-us/help/4464619/windows-10-update-history

[#17]

Thanks for replying, but this is not fixing anything @Dave Patrick 

I would like if you have the steps how to fix it

[#18]

It may be currently blocked (based on article), but again this is a wild guess. I'd suggest starting a support case here with product support.

https://support.microsoft.com/en-us/hub/4343728/support-for-business

[#19]

this is pay support? @Dave Patrick 

[#20]

@LaythServpro 

Inplace upgrade does only work within editions - Don`t know about upgrading EVAL versions.

How Long does EVAL versions work before time bombed?

Best Regards

[#21]

Know I know EVAL Versions only work 180 days! I assume, this Version you could not inplace upgrade!

[#22]

The issue was, in fact, the fact we were attempting the upgrade of the evaluation version. Upon applying a valid license for the current version, Windows installer replaces some core components (restart required), after which the in-place upgrade to Windows Server 2019 worked and allowed retaining of files (and the AD domain data). Hope this helps someone!

[#23]

I'm going thru the same situation, have a 2016 Server Standard Eval and wanted to upgrade to 2019 Server Standard Eval, apparently is not possible to do without a bare metal install.

Used dism /online /get-currentedition to determine the current edition, ServerStandardEval
Used dism /online /get-targeteditions and got ServerStandard as the target, no eval.

Don't have the official MS media, just have the eval download.

[#24]

@mactechTried to upgrade the EVAL to Standard on a test VM using the following command:

dism /online /set-edition:ServerStandard /productkey:WC2BQ-8NRM3-FDDYY-2BFGV-KHKQY /accepteula

It ran overnight and apparently the version was updated but Windows can't be registred because is a public key and don't know what running an unregistered version prevents me to do.

Tried to run the 2019 EVAL install and got to the same screen, can not keep my files so I cancelled.

I'm out of ideas.

[#25]

That's correct, the TechNet server evaluation media cannot be used to perform an in-place upgrade. You'll need to use licensed media for this purpose.

[#26]

@Dave Patrick  Only have they product keys, do you know where I can get the licensed media?

[#27]

The reseller should also provide the installation media. If in the case of volume media you may be able to logon to volume center and download.

https://www.microsoft.com/Licensing/servicecenter/default.aspx