@Matthew Miller
Thank you for posting this in Microsoft Q&A.
As per your description above I see that you are unable to do soft match for 2 accounts from on-premises to Azure.
I also understand that both these accounts in Azure AD has admin roles assigned.
By default, Microsoft Entra Connect isn't allowed to soft match a user object from on-premises AD with a user object in Microsoft Entra ID that has an administrative role assigned to it. THIS IS BY DESIGN BEHAVIOUR.
You can also refer below article,
https://learn.microsoft.com/en-us/entra/identity/hybrid/connect/tshoot-connect-sync-errors#description-7
To resolve the issue that you are facing, remove Admin roles for both users in Azure portal. Now delete newly created accounts in Azure AD manually. trigger a delta sync Entra connect server.
The next sync cycle will take care of soft-matching the on-premises user to the cloud account because the cloud user now no longer has an admin role.
Do let us know if you have any further questions.
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