Hi @Michael Jaszczur,
As this is the expected behavior that emails sent to proxy addresses will be delivered to the primary email address,
if the purpose is to have emails be delivered to both email addresses of this guest user, to me we may need to remove the additional email address from this guest user.
You can remove the additional ******@freedomains.com email address from this guest via Exchange Online Powershell.
The general steps are:
1.connect to Exchange Online Powershell with an account which has Exchange admin permission
2.run the following cmdlet to check the current email addresses of this guest
Get-mailuser guest | fl Displayname,PrimarySmtpAddress,EmailAddresses
3.run the following cmdlet to remove the proxy address from this guest
Set-Mailuser guest -EmailAddresses @{Remove="smtp:******@freedomains.com"}
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