Upgrading Windows 11 on ESXi 6.5: A Step-by-Step Guide

TL;DR: If automatic updates aren’t upgrading your Windows 11 VM on ESXi 6.5, you can manually upgrade using the latest ISO. Download the ISO from aka.ms/downloadwindows11, mount it, and run D:/setup.exe /product server in Command Prompt (replace D: with your ISO drive letter). Do an in place upgrade and as always back up your VM before proceeding.

In a previous post, we walked you through installing Windows 11 on ESXi 6.5. Now, as Windows continues to release major updates, you might find yourself needing to upgrade your Windows 11 version, such as moving from 21H2 to 23H2. However, what I have found is that they might not show up as windows updates. No worries though you can just

Step-by-Step Upgrade Process

Here’s a comprehensive guide to manually upgrading your Windows 11 installation using an ISO file. This method has been tested on a Windows 11 Pro 21H2 virtual machine running on ESXi 6.5 and successfully upgraded it to 23H2. Your experience may vary based on your specific setup, but this should provide a solid foundation.

1. Download the Latest Windows 11 ISO

  1. Visit the Microsoft Download Page: Go to aka.ms/downloadwindows11.
  2. Select ISO Download: Scroll down the page and select the option to download the Windows 11 ISO file instead of the installer.
  3. Choose Your Language: Follow the prompts to select the language based on what you have installed.
  4. Download the ISO: Save the ISO file to your downloads.

2. Prepare for the Upgrade

  1. Mount the ISO: Open/mount the ISO, you can do this by trying to open it like any other file.
  2. Identify the Mounted Drive: In File Explorer identify the drive letter assigned to the mounted ISO. This is typically D: but it can vary based on partitions and connected drives.

3. Running the Upgrade
DO NOT RUN SETUP DIRECTLY IT WILL FAIL!

  1. Open Command Prompt: Open Command Prompt as an administrator. You can do this by right-clicking the Start menu and selecting “Windows Terminal (Admin)” or “Command Prompt (Admin)”.
  2. Execute the Upgrade Command: In the Command Prompt window, type the following command, replacing D:with the actual drive letter of your mounted D:/setup.exe /product server
  3. Start the Upgrade: Press Enter to run the command. This will start the installer with the checks for CPU, TPM and other features disabled.

4. Complete the Installation

  1. Follow the Installer Prompts: The Windows Setup will guide you through the installation process. Select the options that best suit your setup, such as keeping your files and apps.
  2. Wait for the Installer to Finish: The installer will say that it is installing Windows Server, that is A-OK it will actually install whatever version you are on, it just says Windows Server so nothing to worry about.
  3. Reboot and Verify: Once the installation is complete, your VM will reboot. After logging back in, verify the upgrade by checking the Windows version in Settings > System > About.
  4. Run Windows Update: After booting it will still have patches and updates that need to be applied. You will need to got to Settings > Windows Update to install these. You may have to reboot and re-install several times to get them all installed.

Conclusion

Upgrading your Windows 11 VM on ESXi 6.5 doesn’t have to be a headache, even if the automatic updates aren’t cooperating. By manually downloading and installing the latest ISO, you ensure your system remains up-to-date with the latest features and security enhancements.

Remember, while this method worked perfectly on my Windows 11 Pro 21H2 VM to upgrade to 23H2, your mileage may vary depending on your specific environment and configuration. Always ensure you have backups before proceeding with major system upgrades.

Happy upgrading, and stay tuned for more tech tips and guides! If you encounter any issues or have questions, feel free to leave a comment below.

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