@Casey Throop Thanks for posting in our Q&A.
I saw a similar case there. This problem seems to be related to the firewall policy. So I suggest to create a new firewall policy with intune, to ensure that it will not block windows update urls, please refer to: https://learn.microsoft.com/en-us/windows/security/threat-protection/windows-firewall/create-windows-firewall-rules-in-intune
Also we can judge which steps have errors by looking at windowsupdatelogs :
https://learn.microsoft.com/en-us/windows/deployment/update/windows-update-logs
Hope it can help.
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