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“I have a host running Windows Server 2025 Datacenter, and I’m migrating virtual machines to this new server. I also want to upgrade one of my servers from Windows Server 2016 Standard edition to Windows Server 2025 Standard edition. Where can I download the ISO for upgrading from 2016 Standard to 2025 Standard?”
AI answer
To upgrade from Windows Server 2016 Standard to Windows Server 2025 Standard, you can download the ISO for Windows Server 2025 from the Microsoft Evaluation Center. This will allow you to perform an in-place upgrade while keeping your original settings, server roles, features, and data.
Make sure to back up your system and important files before proceeding with the upgrade.
For detailed instructions on how to perform the in-place upgrade, you can refer to the guidelines provided by Microsoft.
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Hello Bob Stubblebine,
I am checking in to see if you have had a chance to review the upgrade path requirements discussed earlier. As noted, the failure with the Evaluation ISO is expected, but the primary technical constraint is that Microsoft does not support a direct in-place upgrade from Windows Server 2016 to Windows Server 2025. You must use valid Volume Licensing or Retail installation media to perform a two-step upgrade, first from 2016 to Server 2019 or 2022, and then to 2025, or proceed with the recommended strategy of migrating roles to a clean Server 2025 deployment to ensure long-term stability.
If the issue has been successfully resolved, please consider accepting the answer as it helps other people sharing the same question benefit too. Thank you!
VP
Hello Bob Stubblebine,
You are correct that the ISO from the Microsoft Evaluation Center is blocked for in-place upgrades on licensed production servers; the installer detects the SKU mismatch and prevents the preservation of applications and settings to avoid converting a production license into a time-limited evaluation version. However, the more critical obstacle you are facing is the upgrade path itself. Microsoft does not support a direct in-place upgrade from Windows Server 2016 to Windows Server 2025. The supported upgrade logic typically extends to the previous two versions (N-2), meaning you can only upgrade to Windows Server 2025 directly from Windows Server 2022 or Windows Server 2019.
To achieve your goal of running Server 2025 on that machine, you must perform a "double-hop" upgrade. You will first need to upgrade the 2016 instance to Windows Server 2022 (or 2019), and once that is complete and stable, perform a second upgrade to Windows Server 2025. Alternatively, since you are already managing a migration scenario, the technically superior approach—which avoids the accumulated registry bloat and potential instability of two consecutive OS upgrades—is to build a fresh Windows Server 2025 VM on your new host and migrate the roles and data (using Storage Migration Service or role-specific tools) rather than upgrading the OS in place.
Regarding the actual ISO download, you cannot use public links for production upgrades. You must obtain the "bits" (non-evaluation ISO) from the Microsoft 365 Admin Center (under Billing > Your Products > Volume Licensing) if you are a Volume License customer, or through the Visual Studio Subscription portal if this is for development/testing. If you purchased a retail license, the link would be in your purchase confirmation or the specific vendor portal. Only the proper Volume or Retail ISO will present the option to "Keep personal files and apps" during the setup process for the supported 2016-to-2022 and 2022-to-2025 paths.
I hope you've found something useful here. If it helps you get more insight into the issue, it's appreciated to accept the answer. Should you have more questions, feel free to leave a message. Have a nice day!
VP
