Hello @Colby ,
Thank you for posting here.
To better understnad our question, please confirm the following information:
How do you configure user roaming profile?
The option 1
The option 2
Via GPO: Computer Configuration\Policies\Administrative Templates\System\User Profiles\Set roaming profile path for all users logging onto this computer
If you set roaming profile on user Properties, on new domain-joined machine, you need to sign in and sign out and sign in again to check roaming profile.
If you set roaming profile via Computer configuration GPO, on new domain-joined machine, you need to sign in and sign out and run command gpupdate /force through CMD, sign out then sign in again to check roaming profile.
Reference
Deploying Roaming User Profiles
https://learn.microsoft.com/en-us/windows-server/storage/folder-redirection/deploy-roaming-user-profiles
By the way, do you have RDP environment?
Hope the information above is helpful.
Should you have any question or concern, please feel free to let us know.
Best Regards,
Daisy Zhou