You will now be "Retail Channel" after doing the free upgrade, even if it was OEM. Run slmgr /dlv from an admin command prompt and see what it says. You'll still likely need to run the trouble shooter to transfer though. You current key will be the generic key you get via the Free Upgrade. ShowKeyPlus
I have many times installed Windows in a VM using physical HDD, then I have just made sure it's activated. After that I have moved the HDD to another device, booting it natively on that hardware and it still stayed activated.
Retail Channel means that install is classed as Retail, not OEM. IMHO, what it means is, if you have issues, contact Microsoft for tech support, not the OEM that originally sold you the PC. Microsoft does not offer tech support for OEM installs. The OEM manufacturer is solely responsible for giving you tech support for their modified custom install. By a Retail copy and Microsoft is your contact for tech support.
With the free upgrade, you could have an OEM PC with say Windows 7. Then you upgrade to Windows 10. But lets say that OEM never shipped that model with Windows 10, should they still be on the hook for tech support? I say no, and that's why it toggles from OEM to Retail. Just my theory as to why.
I just don't know what to tell you? My gut tells me that shouldn't happen. But, I've had numerous installs that got a DL when I think they shouldn't have. Before the AU, my Education installs would show as "Activated with a Product code", no Digital License. They were installed and activated with my MSDN keys. After the AU they all switched to DL's. I think it was the AU, it was one of the major builds. Before that, if I reinstalled, on the same hardware, I had to enter a key to activate. If I did a skip key they wouldn't activate. There was no free upgrade to Education so they never ever got a DL. Then Microsoft changed things and just about every PC on the planet, OEM or Retail, now gets a DL. Even my Enterprise installs that were installed with my MAK MSDN keys toggled to a DL. Before that, it was the same deal as Education. I had to enter a key to activate and they showed as "activated with a product code.
In a properly activated Windows not using a volume license key - whether it be 7, 8 or 10 - I have never seen anything but Retail Channel listed in slmgr /dlv, even on computers with the software load from the factory still in place. Think about it - to Microsoft, any Windows activated by the end user is retail, OEM version or not. When Dell sells a computer to an end user and that end user activates Windows, that is a retail sale. That doesn't change who is responsible for tech support based upon the EULA though. Microsoft sold the Windows 10 Dell at wholesale. Dell turns around and sells the license to the end user at retail. Since the OEM Windows 10 was sold to Dell with the understanding, according to the EULA, that Dell would not be the end user, but would use the license in the course of a retail business. then it makes sense it activates on the "retail channel".
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