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MicrosoftMichaelChapman Without more info, it's hard to say if this is a common scenario. What we see a lot is low disk space issues causing the upgrade to fail. Or a Safeguard Hold that causes it to not be offered. In this case, there also may be a conflict between policies being offered via Intune / AD / ConfigMgr.
I don't want to say that you have to repair the Windows Update agent, but if you haven't tried that on one of the devices, it couldn't hurt to try. You also may want to open a ticket, so they can gather logs.
Thanks Joe. We do have some safeguard holds on drivers and some low disk space issues, but there are a lot that don't have even a medium risk reported. I've followed official guides and community posts for fixing Windows Update on some but these haven't helped. I've done my best to retire any legacy GP objects and ConfigMgr policies for updates, but I'm worried there are tattooed settings in their registries. Are there any keys in particular that I should check?