OK, then. MS has changed the language around who’s eligible to upgrade from prior editions to the May 2019 Update (aka 1903). Now, a safeguard hold blocks 1903 upgrade for affected PCs. All other PCs will get 1903 if they click “Check for Updates” in Settings → Update & Security → Windows Update. This resolves long-standing confusion over who gets the upgrade, and who has to wait. The short version is: if your PC is NOT subject to a known issue that appears in the Windows 10 Health Dashboard, the upgrade goes through. Those PCs subject to one or more such issues must wait until they’re resolved. Now, if only MS would be kind enough to report which such issues apply to blocked machines! Here’s the explainer from the afore-linked Health Dashboard page:
A safeguard hold is present when you click “Check for updates” and aren’t offered 1903. This applies even if you would otherwise be eligible, or expect that upgrade.
[Source: Windows 10 Health Dashboard | Click Image for full-sized-view]
If Safeguard Hold Blocks 1903 Upgrade, Then What?
You wait until Microsoft releases a fix that addresses the safeguard hold(s) on the target PC. Once addressed, users can make manual downloads and upgrades for the May 2019 Update (feature upgrade). I’m glad to see that Microsoft has clarified and codified what many of had figured out by hook and by crook on our own. Right now, 14 items make up the list of potential issues that could lead to safeguard holds for Windows 10 PCs.
Of course, one can still apply the upgrade anyway despite the block. There are two ways to do this: one is to visit the Download Windows 10 page, then click the “Update now” button at the top of that page to run Microsoft’s Update Assistant. Another is to download and mount a Windows 10 ISO for 1903. After that, run the setup.exe file at the root of that volume.
I’ve done this for four of the 5 PCs I currently have running Windows 10 1903 at the office. I did experience a couple of minor installation glitches along the upgrade path. But all machines upgraded successfully on either the first or second try. In fact, 4 of those 5 made it on the first try, and only one required a second. So far, the 1903 installer and subsequent stability are winners in my book.