When I added his email address, I received the following warning:
Connection, Recipient, and Sender Filtering must manually be enabled on specific SMTP virtual server IP address assignments as they are not enabled by default. For more information on how to enable any of the above filtering types, read their associated help.
You need to enable sender filtering on each IP address of each SMTP virtual server that you have.
For each server, Expand the Admin group, then Server, then Protocols, then SMTP, then right click on Default SMTP Virtual Server and click on properties, then click on the Advanced button and, then click on Edit and tick the Apply Sender Filter checkbox.
In most cases you will have (All Assigned) for the IP address entry, however you have have manually specified multiple IP addresses for the SMTP VS, then you'll need to modify each IP address entry.
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