Problem upgrading windows server 2016 to 2019

Question

Hello,

I am trying to perform a in-place upgrade of windows server 2016 (standard version) to 2019 (idem) non-Azure. I have downloaded the iso (eval, I can't find another type) from the MS repo abd when I launch the upgrade, the option to save my data/files, is greyed (non-accessible) : from what I've read, I need to download a trial version (done) and then register my license key to upgrade the windows server 2019 trial version to standard. Does anyone have an idea of the problem and a solution please ?

Answer 1

Hi Clement Mezerette,

to perform an in-place upgrade while keeping your data and files, you will need to have a valid license key for Windows Server 2019 Standard edition.

You can purchase a license key from Microsoft or a Microsoft reseller, and then use that key to activate the trial version of Windows Server 2019. Once activated, you should be able to perform an in-place upgrade while keeping your data and files.

Alternatively, you can perform a clean installation of Windows Server 2019 and then migrate your data and files from the old server to the new server. This may take more time and effort, but it will ensure that you have a clean and stable installation of Windows Server 2019.

Regards,

Lei

Answer 2

Hi Lei Tao,

Thank you for your prompt reply. I've already bought a licence key which I haven't had a chance to enter because when I launch the windows server 2019 installation procedure (via setup.exe from the ISO from MS), the option to save all my data is greyed out.

If I understand correctly, I need to activate my licence key before running the setup.exe to have the option available : where? In windows settings ? Via a prompt command? Can I activate a licence for win server 2019 when I'm on win server 2016 ? Everything is done on the same server and I can't lose my data...

Answer 3

No, you need to install Windows Server 2019 before you can activate your system.

Here are some methods you can try:

1.Free Up Disk Space. Make sure you have enough free disk space on your server. The upgrade process might require additional space for temporary files. If your disk is nearly full, consider freeing up space before attempting the upgrade.

2.Check System Requirements. Ensure that your hardware meets the system requirements for Windows Server 2019. Please refer to this link:

Hardware requirements for Windows Server | Microsoft Learn

Best Regards,

Hania Lian

Answer 4

Hello,

Thank you for taking the time to reply, but it doesn't answer the problem: I bought a standard Windows 2019 licence to upgrade my company's Windows Server 2016 (standard) for a in-place upgrade ; I have disk space available - 40G for the C partition, and more than 700G on the other partitions - and when I run the setup. exe of the iso file downloaded from the Microsoft site (the only one available is an evaluation version that I should activate with my key once installed), the option to keep my files and data is greyed out: Why? And how to fix this problem ? Please :)

Answer 5

Hi Clement Mezerette,

it may be due to the fact that you are using an evaluation version of the ISO file instead of the full version of the ISO file.

In order to fix this, you need to use the full version of the ISO file to run the installer.