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Any update on this? It's past EOL and I'm still stuck on 1909. Now Windows Update says "You're not up to date" and "Your device is missing important security and quality fixes." but "Check for updates" doesn't fix it.
The issue is most likely outdated drivers. If you open Event Viewer (right-click "Start" and select "Event Viewer") and drill down to "Applications and Services Logs" > "Microsoft" > "Windows" > "WindowsUpdateClient" > "Operational", it should list what the upgrade does not like. In the post I referenced above, there were two drivers causing the issue. One required an update from the Dell site, the second could only be gotten directly from Intel (unless Dell has subsequently provided the appropriate update). See if the Event Viewer is referencing those same drivers.