Outlook seems to have issues with some of our spam filters getting flagged as spam. You will want to ensure that the SMTP Authentication is checked in the Outgoing settings.
As a further test, please have the email sent via webmail to see if it goes through. If so, it is definitely the Outlook. If it does not go through, please contact our Live Support at firstname.lastname@example.org with that request. Be sure to validate your account with either the last 4 digits of the credit card on file, or the current Account Management Panel (AMP) password.
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