forward exchange email to external contact from external source

Posted on 2007-08-07
Last Modified: 2008-12-04
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.

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

Type: Contact: Joe External
Under email-addresses:
Under Exchange General - E-mail:

Now, when an internal person - say Mary Jane - - 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 to either (user mailbox) or (directly to the contact) - neither email gets forwarded to

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.
Question by:jon_m_obrien
    LVL 11

    Accepted Solution

    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..
    LVL 58

    Assisted Solution

    It could also be that the setting in either the contact or main user is set to only allow authenticated users to send mail to that user. Check that box isn't ticked and try again. In theory, GFI shouldn't be blocking it since it is just a normal mail which arrives in the mailbox then exchange sends another out to the external contact. I wouldn't say it's strictly relaying since it goes into the mailbox too, but GFI might be considering it as such and there's some special rule blocking it?.

    The setting is in exchange general > delivery restrictions and marked "From authenticated users only". Also check that Accept messages "From everyone" is selected. Verify those settings on both user and external contact.

    Author Comment

    Let's see.
    On the contact - Accept messages: From everyone.
    Same with the user.
    And I created a new user and new contact specifically to test.

    mohdabsar - that seems to make sense, I wondered why it would forward from internal but not external, and if you say you specifically had the same issue with trend - detecting the originator and the destinator as both being external and treating it as spam, then that sounds to be the right path.

    I figured it shouldn't be Exchange itself treating it as a relay'd message even though relaying is denied "excpet computers that authenticate" as I should hope Exchange is intelligent enough to realise an email forwarded to a contact is not relaying.

    As I said, I did not install GFI and know nothing about it. I did have a look at some logs I could see, and configuration options, but saw nothing resembling what I'm after, I didn't see any indication of anything blocked. But with your encouragement I will look further into the GFI side.


    Author Comment

    There seems to be GFiMailEssentials and GFiMailSecurity... guess I'll have to look into both.
    LVL 58

    Expert Comment

    Nope, sending to an exchange mailbox and then that being forwarded is strictly NOT relaying so your relay settings shouldn't be causing the problem.

    If GFI isn't the fault, there's always OWA!

    Author Comment

    No... I've just jumped on another server (2003 Std Server + Exchange 2003 Server)
    and created a new contact same as original post.
    Same thing - internal email forwards to external contact email address.
    email from external does not.

    This server does route its email through a Barracuda filter, but I am starting to wonder if it's not a GFI / Barracuda issue, but a Microsoft issue? I guess I am just going to have to go jump on a third server that has no external mail filtering and see.
    LVL 58

    Expert Comment

    That sounds like the best troubleshooting plan!

    Author Comment

    Dang - works perfectly.

    So must be a GFI / Barracuda filter!

    Argh - anyone out there use GFI and know hoe to get it to allow "relaying" to a particular domain? I tried adding in a whitelist record. No luck. Unless I need to restart a service.

    I'm just shooting in the dark. Anyone got any specific instructions please?

    LVL 11

    Expert Comment

    Have you checked the GFI FAQ..check on thier website.
    Or is it possible for you to give them a call

    Author Comment

    Tried Live Chat. How completely useless. Tried searching Knowledge Base...

    Anyway, I saw there was a section in GFI for "Mail Monitoring" where you monitor an account and it forwards a copy to someone.
    So any email sent To: "" is now forwarded to joeexternal.

    Essentially it looks like the same thing as an Exchange contact, except controlled from GFI as the email comes IN to GFI before going through Exchange.
    I've left the Contact forwarding as well as I haven't tested yet if GFI will pick up internal email - I just sent an internal email - only one copy came through - might test later if I remove the contact if GFI will pick it up internally.

    But for now, it is working.

    mohdabsar seems to have been right on the first response with the cause of the problem and explained the REASON for the problem which enabled me to find the solution, so should get most points.
    tigermatt helped with suggestions keeping me on the right path so want to give some points to you too.

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