Problem sending email to external contacts from Exchange 2010

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.
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Vaseem MohammedCommented:
what does the rule says?
what is its logic?
mlmslexAuthor Commented:
Rule is as follows:
Step 1: "with specific words in the subject or body" (words defined), "from people or public group" (defined as existing contact - our reporting system which sends out emails)

Step 2: "forward it to people or public group" (defined as the SMTP contact from the GAL in Exchange)

End of rule.

I've even turned off the "from people or public group" - hasn't made a difference.
Simon Butler (Sembee)ConsultantCommented:
The messages are probably seen as spoofed by the filtering company. I don't think Exchange will change the headers, so the original from line stays in place. If the filtering company is checking for spoofed messages, then they will block them. Not a lot you can do about it, as spoofing is one of the biggest spam problems on the internet.


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