Windows 10: Air-Gapped Windows 10 v.1909 upgrade

Hello,


I manage an air-gapped, non-networked Windows10 workstation that is currently v. 1909. I understand that version 1909 is going to be going out of support on 05/11/2021. I need to know how to upgrade to version 2004 or 20H2 in order to remain compliant with security updates for this system. The system cannot be connected to the internet. I also need to know that the upgrade process upgrades the OS without removing or resetting security settings currently on the system. Thank you in advance for your help.

:)

 

Air gapped system: Windows 8.1 to Windows 10 upgrade

I have an air-gapped (I.e., no external physical or wireless communication) system running W8.1 - I note internet connectivity seems to be mandatory for availing of this free upgrade.

Are there any options available for upgrading my system?

 

Windows 10 Upgrade Air Display Error

I have read numerous posts regarding the Air Display error preventing an upgrade to Windows 10, stemming from the Air Display app. On the website they fully disclose they are not 10 compatible.

So, removed the app, removed from device manager (must choose to display hidden) and still no luck. I understand there is a "list" that is run for compatibility and is updated only once per month or so, but the last time my list was updated was back in
April! The list that I am referring to is the one that appears when you choose the 10 upgrade icon and it gives you the Air Display non-compatibility error, it refers to a list that apparently still has Air Display on it, which prevents the upgrade. Sooooo,
any other suggestions from the warriors that have licked this problem?

Thanks!

 

Windows 10 Activation of an Air Gap or Offline Network

I have an air gap network. This network has no Internet connectivity and, because of security requirements, will not ever have Internet connectivity. I need to upgrade the desktop PCs on this network to Windows 10. The Windows 10 upgrade installs correctly.
However, I am running into problems when I try to activate the installation. I have tried using the specific Windows 7 Pro OEM license that came with the machine from Dell as the activation key but this does not work. Does anyone know how I can perform
an offline activation of Windows 10? I am testing the Windows 7 to Windows 10 upgrade on one machine, but if I can get this to work correctly, I'll need to activate approximately 40 machines.