Windows 11 IoT Enterprise LTSC 2024 Evaluation cannot be converted to the licensed edition while keeping applications

Question

Windows 11 IoT Enterprise LTSC 2024 Evaluation cannot be converted to the licensed edition while keeping applications

alberto televalentin 0

Hello,

I installed Windows 11 IoT Enterprise LTSC 2024 Evaluation, downloaded directly from Microsoft’s official Evaluation Center, on two computers used for professional audiovisual production.

During the evaluation period, I installed and configured dozens of professional applications, hardware drivers, databases, video and audio devices, codecs, plugins, network settings, and production-specific configurations.

My intention was to evaluate the operating system and, once compatibility had been confirmed, purchase legitimate Windows 11 IoT Enterprise LTSC 2024 licenses and activate the existing installations.

My current edition is:

IoTEnterpriseSEval

TIMEBASED_EVAL channel

I obtained the full non-Evaluation Windows 11 IoT Enterprise LTSC 2024 installation media and launched setup.exe from within the current Windows installation.

I selected:

Windows 11 IoT Enterprise LTSC

However, the option “Keep personal files and apps” is disabled. Windows Setup displays the following message:

“Your files, apps, and settings can’t be kept because you’re installing an edition of Windows that’s different than the one you’re currently using.”

The installer only allows me to keep personal files, which would delete all installed applications and settings.

This means that purchasing a legitimate product key does not solve the problem, because IoTEnterpriseSEval cannot apparently be converted to IoTEnterpriseS through an in-place upgrade while preserving applications.

I would like an official answer from Microsoft to the following questions:

Is there any officially supported method to convert IoTEnterpriseSEval to IoTEnterpriseS while keeping all installed applications, drivers, files, and settings?
Can a legitimate MAK, PKEA, ePKEA, OEM, or volume license key perform this conversion without reinstalling Windows?
Is there any supported DISM, Windows Setup, provisioning package, or edition-upgrade procedure for this scenario?
If no conversion path exists, why is this limitation not clearly and prominently stated before downloading and installing the Evaluation edition?

A 90-day Evaluation edition reasonably suggests that users can test the product and later purchase a license without rebuilding the entire system. In this case, Microsoft allows users to fully configure the operating system but apparently requires a new installation to move to the licensed edition.

I currently have two professional production computers affected by this issue. Reinstalling Windows would require rebuilding two complete audiovisual production environments from scratch.

I am not requesting unofficial activation methods, registry modifications, third-party scripts, cracks, or external KMS servers. I am requesting an officially supported and legitimate Microsoft solution.

If no supported conversion method exists, Microsoft should add a clear warning to the Evaluation Center download page and installation process stating:

“This Evaluation edition cannot be converted to the full licensed edition while preserving installed applications and settings. A new installation may be required.”

Thank you.

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Answer 1

Brian Huynh 3,815 Microsoft External Staff

Hello, thank you for posting in the Microsoft Q&A community.

The main reason activation or key entry fails on Evaluation media is that evaluation builds (SKU: IoTEnterpriseSEval) are designed strictly for temporary 90-day testing purposes. Evaluation media contains hardcoded licensing restrictions that prevent direct conversion to full production licenses simply by entering a Multiple Activation Key (MAK), KMS key, or OEM product key via Settings > System > Activation or slmgr.vbs.

Depending on your goal, please follow the resolutions below:

Solution: To permanently activate the operating system with a production key, you must transition from the Evaluation SKU to the standard production SKU (Windows 11 IoT Enterprise LTSC 2024):

Obtain the full production ISO for Windows 11 IoT Enterprise LTSC 2024 from your Volume Licensing Service Center (VLSC), Microsoft Admin Center, or authorized OEM distributor.
Mount the ISO file directly within your current Evaluation installation.
Launch setup.exe to perform an In-Place Upgrade / Repair Install, ensuring you select Keep personal files and apps.
After the installation completes, open Command Prompt as Administrator and execute the following to apply and activate your license:

slmgr.vbs /ipk <YOUR_PRODUCT_KEY>
slmgr.vbs /ato

If you are currently evaluating the platform and require additional testing time before deploying production media, you can reset the 90-day evaluation period up to 3 times (providing up to 270 days of total evaluation time):

Open Command Prompt as Administrator.
Run the rearm command:

slmgr.vbs /rearm

Restart the computer for the extended evaluation counter to take effect.

I will follow up on this thread to ensure your issue is resolved. If this helps, please consider hitting "Accept answer".

For official details regarding licensing and deployment, please consult:

alberto televalentin 0 Reputation points

2026-07-28T07:15:00.1+00:00
Hello Brian,

Thank you for your reply.

However, I have already followed the exact procedure you described, and Windows Setup does not allow me to select “Keep personal files and apps.”

My current installation is:

Edition: IoTEnterpriseSEval

Channel: TIMEBASED_EVAL

OperatingSystemSKU: 207

I mounted the full non-Evaluation Windows 11 IoT Enterprise LTSC 2024 en-US ISO from within the running Evaluation installation, launched setup.exe, and selected:

Windows 11 IoT Enterprise LTSC

However, on the “Choose what to keep” screen, “Keep personal files and apps” is disabled.

Windows Setup displays:

“Your files, apps, and settings can’t be kept because you’re installing an edition of Windows that’s different than the one you’re currently using.”

The screenshot showing this message is attached to my original question.

Your instructions state that the production key should be installed only after the in-place upgrade has completed. Therefore, according to those instructions, the absence of a production key during Setup should not be the reason why the option is disabled.

Could you please clarify the following:

Have you personally verified that an in-place upgrade from SKU 207 (IoTEnterpriseSEval) to SKU 191 (IoTEnterpriseS) preserves installed applications?

Must Setup actually be launched with a production key before the compatibility check, for example:

setup.exe /pkey XXXXX-XXXXX-XXXXX-XXXXX-XXXXX

If the product key must be supplied before Setup, why does your procedure state that the key should be installed only after the upgrade?

Could you provide an official Microsoft document that explicitly confirms that IoTEnterpriseSEval can be converted to IoTEnterpriseS while preserving applications and settings?

Does the production ISO obtained from VLSC or the Microsoft Admin Center contain different upgrade compatibility rules from the full non-Evaluation ISO I tested?

I do not want to purchase two licenses until Microsoft confirms a reproducible and officially supported method that preserves all installed applications and settings.

Thank you.
Brian Huynh 3,815 Reputation points Microsoft External Staff

2026-07-28T08:29:55.8766667+00:00

First, I want to sincerely apologize if previous replies suggested that an in-place upgrade from an Evaluation edition to a Production edition was possible while keeping your applications and settings.

Let me address your questions directly:

1.I can personally confirm that the block you are experiencing is intentional. The Windows Setup engine reads the current Operating System SKU (207) and matches it against the compatibility matrix (the cbs engine). Because SKU 207 is flagged as an Evaluation/Time-based SKU, Setup permanently disables the "Keep personal files and apps" option to prevent evaluation timebomb registry keys from polluting a production environment.

2.No. Supplying a product key via the /pkey switch will not bypass this restriction. Setup blocks the migration based on the Source OS (your current Evaluation installation), not the target key.

3.Performing an in-place upgrade first and applying the key later is only valid for standard production edition upgrades (e.g., upgrading from Windows 11 Pro to Windows 11 Enterprise). That procedure is invalid for Evaluation editions.

4.Microsoft's official stance across all Windows Client Evaluation software (including Windows 11 Enterprise and IoT Enterprise LTSC) is that moving to a production release requires a Clean Installation.

5.No. Regardless of where you source the Production ISO (VLSC, Microsoft Admin Center, or Visual Studio Subscriptions), the underlying Windows Setup binaries and compatibility matrix are identical.

I know this is not the news you were hoping for. Because there is no workaround. You will unfortunately need to rebuild the environment via a clean installation using the Production ISO (SKU 191) once you acquire the proper licensing.

In the meantime, you can continue using the slmgr.vbs /rearm command (up to 3 times) to extend your current evaluation period while you back up your databases, project files, and application configurations.
alberto televalentin 0 Reputation points

2026-07-28T10:01:08.0833333+00:00

Thank you for the clear clarification.

This confirms that the Evaluation edition cannot be converted to the Production edition while preserving installed applications and settings, regardless of the production ISO source or product key.

I appreciate that you corrected the previous information.

However, this limitation should be stated prominently on the Microsoft Evaluation Center download page and during installation. A user should be clearly warned before configuring a production environment that purchasing a legitimate license later will still require a clean installation.

I currently have two professional audiovisual production computers affected by this limitation.

Please consider escalating this feedback to the Windows IoT documentation and product teams so that future users receive a clear warning before downloading and installing the Evaluation edition.

Thank you.