We have a small Exchange 2010 server, with both inbound / outbound (via SmartHost) spam/virus filtering performed by an outside company.
We have certain emails (determined by Exchange-based rules) that we'd like forwarded to an external SMTP contact. We've defined the contact in Exchange.
From outlook, if we send an email directly to the contact (either by typing the email address manually or by typing the alias into the To: field), the messages send just fine. We can also forward email (via Outlook) directly to the contact.
When trying to send (forward to) that same contact, via a rule, the messages aren't ever received.
You would think it's just that the rule isn't working but I don't think that's the case.