Question : forward exchange email to external contact from external source

Hi, I've set up Contacts (previously Alternate Recipients) in Exchange 2003 Server (SBS2003), and forwarding a copy of email to the contact. When an Internal person sends an email, it gets forwarded to the external address, but when an email comes in from outside, it does not.

Scenario:
Type: User: Joe Bloggs
email address: [email protected]
Account properties - Exchange General - Delivery Options - Forwarding Address - Forward To:
    JoeExternal
Deliver to both forwarding address and mailbox is ticked.

Type: Contact: Joe External
Under email-addresses: [email protected]
Under Exchange General - E-mail: SMTP:joeoutthere@someotherdomain.com

Now, when an internal person - say Mary Jane - [email protected] - emails Joe Blow, the email is forwarded to Joe External and gets to Joe Out There's outside mailbox.

But if I send an email from somewhere else - from [email protected] to either [email protected] (user mailbox) or [email protected] (directly to the contact) - neither email gets forwarded to joeoutthere@someotherdomain.com.

Why not? I cannot find anywhere that distinguishes whether an email to a contact originates from inside or outside. Please help.

PS. The email is routed through GFI Mail Essentials - I didn't set it up, it was already there. Could that make a difference? I don't see how it would distinguish an email forwarding to a contact from internal vs external and even if so, why it would treat it any different.

Answer : forward exchange email to external contact from external source

The reason could be that GFI is considering as relaying etc, the header of mail which is sent from external account and the final destination which is also external e-mail address and this could be reason in your scenario for blocking the mails...
Check the GFI logs you should find it blocked there and then check the appropriate rule/configuration and modify it according to your need.

I have same scenario with trend IMSS..