Hi Scott, Welcome in Community
The ESU eligibility check relies heavily on the Connected User Experiences and Telemetry service.
Run the following from an elevated Command Prompt or PowerShell as administrator:
sc.exe config DiagTrack start= auto
sc.exe start DiagTrack
Now trigger the silent evaluation executable:
cmd /c ClipESUConsumer.exe -evaluateEligibility
Then check if the evaluation succeeded by querying the registry:
reg.exe query "HKCU\SOFTWARE\Microsoft\Windows NT\CurrentVersion\Windows\ConsumerESU"
You are looking for ESUEligibility to equal 0x2 and ESUEligibilityResult to equal 0x1. If those match, go back to Windows Update and try enrolling again.
Let me know how it goes
Elvis