I decided to test the Windows 10 upgrade thing a couple of weeks ago. I’d heard (well, read) some people saying that the free upgrade, which extended well beyond the official one-year period in practice, had finally ended, and that upgrades were no longer automatically activating. Others reported it still worked.
I decided to test it on one of my VMs on my Core 2 Duo laptop, running Windows 7 as a guest (Linux Mint 18.3 host). The Windows 7 guest is activated, so if the free upgrade works, it should show 10 activated too.
I grabbed my old .ISO (the same one I used to perform the initial upgrade when I tested 10 in 2015, which means it’s for 10240/1507) and upgraded it (on a clone of my 7 VM; I am not giving up 7!). It upgraded without any problems, and it shows that it is activated in 10.
So far, so good. So what? (Great album!)
It immediately installed a few updates for 1507, then began downloading the update to 1803. It failed the first time, as I did not have enough room in the VM’s virtual hard drive. I tried plugging in my external HDD and pointing Windows Update at it, and it seemed to be working, but it didn’t (the details of why are fuzzy).
I increased the size in the VM for 10, and let it try again. It began to install the upgrade, but then something happened on the reboot and it reverted to 10240 again. I hit the check for updates button to try again, and this time it downloaded and rebooted into the “This will take a while, don’t turn off your computer” screen. It froze at 7%… no flashing of the virtual HDD light, no sign of activity, the little spinner thing onscreen frozen, the CPU usage pegged at 100%, with the laptop fan whirring noticeably. After a few hours of waiting, I reset the VM.
It rebooted, then went to “reverting to your previous version of Windows.” And then it froze once again. After a long wait to make sure it was really frozen, I reset it.
It rebooted, and went to a black screen. Same deal… no HD activity, CPU pegged, no signs of actually doing anything forever. Reset it again, after dutifully waiting in case it was really doing something.
The next time it said “reverting to your previous version” again, and this time it did actually revert to my previous version.
Windows 10 did eventually come back up, still at 10240. I checked for updates again, and it found the upgrade to 1803 again, so I let it try again. The second try went about like the first… froze at 7%, then froze again, then again, and then it gave up and reverted to 10240 again.
Now it says that it’s up to date when I check for updates, in 10240. It installs the frequent updates for Defender, and that’s it. It does not find the 1803 update anymore.
Now, I know there are ways I can force the issue with updating (using the media creation tool to make an .ISO, then upgrading in place), but one of the points of this exercise was to see how the experience looks to a regular user, and it’s not good. It’s telling me that a version of Windows 10 that gets no more security updates is “up to date,” which it most certainly is not. It already tried the 1803 update and concluded it’s not gonna work, I guess, but it’s not smart enough to try to update to a 16xx or 17xx first and to go from there to 1803. Given that you can’t get ISOs of those versions officially anymore, I would guess that MS considers them to not exist, so it’s update all the way or nothing.
It’s still claiming 10240 is up to date, even today, after this month’s patches are out. It downloaded and installed the MSRT and the Defender update, and that’s it.
Dell XPS 13/9310, i5-1135G7/16GB, KDE Neon 6.2
XPG Xenia 15, i7-9750H/32GB & GTX1660ti, Kubuntu 24.04
Acer Swift Go 14, i5-1335U/16GB, Kubuntu 24.04 (and Win 11)