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currently I have the following running:

Name: Windows(R), ServerStandardEval edition
Description: Windows(R) Operating System, TIMEBASED_EVAL channel
Product Key Channel: Retail:TB:Eval

and bought a Windows Server 2016 Essentials key. However, changing the product key via System fails with:

screenshot

Executing

Cscript.exe %windir%\system32\slmgr.vbs /ipk <***KEY***>

returns

Error: 0xC004F069 On a computer running Microsoft Windows non-core edition, run 'slui.exe 0x2a 0xC004F069' to display the error text.

And slui.exe 0x2a 0xC004F069 Comes up with

Code: 0xC004F069
Description:
The Software Licensing Service reported that the product SKU is not found.

Anybody having an idea why this fails? This instance was now running for a while and I decided to finally buy it.

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I can't add this as a comment but have you tried

dism.exe /get-targeteditions

To get what editions are available to be upgraded to. And assuming Server Essentials is available running the following but changing ServerDatacenter and the product key to the appropriate respective values

dism.exe /online /set-edition:ServerDatacenter /productkey:00000-00000-00000-00000-00000 /accepteula
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NOT THE ANSWER

@Muh Fugen

dism.exe /online /get-targeteditions returns:

Editions that can be upgraded to:
Target Edition : ServerStandard
Target Edition : ServerDatacenter

Executing dism.exe /online /set-edition:ServerDatacenter /productkey:MY_KEY /accepteula returns

Error: 1605 The specified product key is not valid for the target edition.
Run this command again with a product key that is correct for the target edition.
The DISM log file can be found at C:\Windows\Logs\DISM\dism.log

However, using the key with a Server 2016 Essentials ISO works pretty fine.

Filtering DISM.log for any errors and warnings results in:

2017-02-03 03:31:21, Warning               DISM   DISM OS Provider: PID=31272 TID=14592 Unable to set the DLL search path to the servicing stack folder. C:\Windows may not point to a valid Windows folder. - CDISMOSServiceManager::Final_OnConnect
2017-02-03 03:31:21, Warning               DISM   DISM Provider Store: PID=31272 TID=14592 Failed to Load the provider: C:\Users\ADMINI~1\AppData\Local\Temp\6C4E064D-7182-415E-B745-2CB7735BB5B4\PEProvider.dll. - CDISMProviderStore::Internal_GetProvider(hr:0x8007007e)
2017-02-03 03:31:23, Warning               DISM   DISM Provider Store: PID=31272 TID=14592 Failed to Load the provider: C:\Users\ADMINI~1\AppData\Local\Temp\6C4E064D-7182-415E-B745-2CB7735BB5B4\EmbeddedProvider.dll. - CDISMProviderStore::Internal_GetProvider(hr:0x8007007e)
2017-02-03 03:31:23, Error                 DISM   DISM Package Manager: PID=31272 TID=14592 Failed opening package Microsoft-Windows-ServerStandardEvalEdition~31bf3856ad364e35~amd64~~10.0.14393.594. - CDISMPackageManager::Internal_CreatePackageByName(hr:0x800f0805)
2017-02-03 03:31:23, Error                 DISM   DISM Package Manager: PID=31272 TID=14592 Failed to get the underlying cbs package. - CDISMPackageManager::OpenPackageByName(hr:0x800f0805)
2017-02-03 03:31:23, Error                 DISM   DISM Package Manager: PID=31272 TID=14592 The specified package is not valid Windows package. - GetCbsErrorMsg
2017-02-03 03:31:24, Error                 DISM   DISM Transmog Provider: PID=31272 TID=14592 Product key is keyed to [ServerSolution], but user requested transmog to [ServerDatacenter] - CTransmogManager::ValidateTransmogrify
2017-02-03 03:31:24, Error                 DISM   DISM Transmog Provider: PID=31272 TID=14592 [Upgrading system]: The specified product key is not valid for the target edition.
Run this command again with a product key that is correct for the target edition.
 [hrError=0x80070645] - CTransmogManager::EventError
2017-02-03 03:31:24, Warning               DISM   DISM Transmog Provider: PID=31272 TID=14592 The selected OS *cannot* upgrade to [ServerDatacenter] - CTransmogManager::TransmogrifyWorker
2017-02-03 03:31:24, Error                 DISM   DISM Transmog Provider: PID=31272 TID=14592 Failed to Upgrade! - CTransmogManager::TransmogrifyWorker(hr:0x80070645)
2017-02-03 03:31:24, Error                 DISM   DISM Transmog Provider: PID=31272 TID=14592 Failed to upgrade! - CTransmogManager::ExecuteCmdLine(hr:0x80070645)
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It is obvious why it didn't work. You bought a Essentials key but tried to upgrade to Datacenter.

I suggest you to get an ISO of the Server Essential Evaluation from the Microsoft Evaluation Center, (clean) install it, run dism.exe /online /get-targeteditions and dism.exe /online /set-edition:ServerEssentials /productkey:YOUR_KEY /accepteula (Replace YOUR_KEY with your Windows Server Essentials product key)

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