I'm planning to do an in-place upgrade of my Windows Server 2016 Standard (with GUI) directly to 2025. I understand that ideally, a fresh install is recommended, but for various reasons, I'm opting for an in-place upgrade. I've also learned that I need to first upgrade to 2019 before moving on to 2025. However, I'm running into a bit of a snag with obtaining the ISO files. The evaluation versions I found won't allow me to keep my files, and although I've ordered the license for 2025 and have that ISO, I'm struggling to find a reliable source to download the 2019 ISO. Does anyone know where I can find the Windows Server 2019 ISO?
5 Answers
You can actually upgrade directly from 2016 to 2025 without needing to go through 2019 or 2022. Just make sure to run the setup.exe from a SYSTEM account to avoid any issues. I once had the upgrade fail before the first reboot on some VMs, but using psexec.exe to run `psexec -i -s d:setup.exe` worked for me!
The evaluation version is still a full version, and you can download it from Microsoft's official site. Here's a link to the 2019 ISO: [Windows Server 2019 Eval](https://www.microsoft.com/en-us/evalcenter/download-windows-server-2019). If the option to keep your files is missing, it may be due to some incompatible server roles or applications that are preventing a clean in-place upgrade.
Honestly, in-place upgrades usually work great without many issues. Just watch out for any weird software that might cause problems during the upgrade.
Check out this link for multiple Windows Server downloads: [Windows Server Links](https://massgrave.dev/windows-server-links). That should help you find the ISO you need.
I haven't encountered many issues with in-place upgrades either, unless there was some odd software running on the server that interfered.
Thanks for the tip! I'll definitely give that a try.