External Email Forwarding Fails
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Thread: External Email Forwarding Fails

  1. #1

    Question External Email Forwarding Fails

    So I have an interesting little problem I'm looking into for one of our clients --

    They're in an Exchange environment. First, the user set his Outlook to forward his mail from his address to another internal email address. No problem. The new mail enters his inbox briefly, then immediately passes on to the forwarded address. Then, he changed it to forward to an external email (his hotmail address in this case). This time, the new mail comes in, and nothing happens; it stays in the inbox. So he tried to send it manually, and it does move into the Sent Items folder, but it never arrives in the destination inbox. He's tested this with several different external email accounts (hotmail, yahoo, and charter), and he experiences the same problem each time. So evidently his mail will only successfully forward to internal email addresses.

    He noted that they had a problem with people forwarding email too often a couple of years ago. He said that he suspects that perhaps whoever resolved that problem back then may have set some sort of restriction in Exchange to prevent them from forwarding anything to external email addresses. However, he says he checked all the Exchange policies, and everything is on a "low" setting.

    So what I did was tinker around with forwarding in Exchange. I'm new to Exchange, so I'm literally learning as I go here, but I managed to create a contact object in AD Users & Computers that contained his hotmail address, then set his user account in AD to forward all email to that object. That worked.

    However, that's also not what he wants. He wants to be able to set up forwarding from his Outlook client instead of having to go through the Exchange server every single time, so turns out there was no point to all that tinkering I did anyway.

    So any ideas? Could there be a setting in Exchange somewhere that's preventing users from setting up external forwarding from their Outlook client aps? Or what else could cause this issue where they can forward inside but not outside?

  2. #2
    AO Ancient: Team Leader
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    He probably needs to be pre-authenticated to Hotmail etc. to be able to do it...

    Did you ever think of using OWA? Then he can get to his inbox from anywhere via SSL whenever he wants...
    Don\'t SYN us.... We\'ll SYN you.....
    \"A nation that draws too broad a difference between its scholars and its warriors will have its thinking done by cowards, and its fighting done by fools.\" - Thucydides

  3. #3
    That didn't occur to me actually. I'll have to recommend that.

    So this is interesting -- I got curious, and tried from my email. Keep in mind this is a client problem, so my Outlook on our network managed by our Exchange server is not set up like theirs. So I set up my Outlook to forward all messages that come from my cell phone back to my cell phone -- so I've set up, from my client ap, a rule forwarding that email to an external account. Tried it out -- I sent an email from my cell to my email, and it showed up as a new message in Outlook, but it never forwarded back to my cell phone. So I can recreate the same problem here on our Exchange network. So I'm wondering -- Is there something about Exchange that overrides forwarding to the outside from being enabled client-side?

  4. #4
    Senior Member RoadClosed's Avatar
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    Is there something about Exchange that overrides forwarding to the outside from being enabled client-side?
    \

    Yes there is otherwise Spammers would eat you alive. They would address a message to your exchange account and use you to Spam away. Chips Ahoy.
    West of House
    You are standing in an open field west of a white house, with a boarded front door.
    There is a small mailbox here.

  5. #5
    Found it -- it's an obscure little checkbox...

    Go into Exchange System Manager --> Global Settings --> Internet Message Format, and right-click Default. Go into the Advanced tab and lo and behold, there's a little checkbox beside "Allow automatic forward".

    Very rare I actually manage to answer my own thread.

  6. #6
    Senior Member RoadClosed's Avatar
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    know the dangers involved in forwarding external mail addresses to external mailboxes.
    West of House
    You are standing in an open field west of a white house, with a boarded front door.
    There is a small mailbox here.

  7. #7
    AO Ancient: Team Leader
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    Then why would you do it...

    OWA works and has been proven quite secure...
    Don\'t SYN us.... We\'ll SYN you.....
    \"A nation that draws too broad a difference between its scholars and its warriors will have its thinking done by cowards, and its fighting done by fools.\" - Thucydides

  8. #8
    I agree, but it's not my network. Note in the above post that email forwarding actually was a problem for them in the past too, so you'd think they'd have learned their lesson then eh? Regardless of whether it's a good idea or not, that's what they want though, and "the customer is always...WRONG!!!!" But oh well!

  9. #9
    Senior Member RoadClosed's Avatar
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    Then why would you do it...
    It's disabled for a reason. I would NOT do it.

    OWA is slick. But I don't use it either.
    West of House
    You are standing in an open field west of a white house, with a boarded front door.
    There is a small mailbox here.

  10. #10
    Senior Member RoadClosed's Avatar
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    Regardless of whether it's a good idea or not, that's what they want though, and "the customer is always...WRONG!!!!"
    In that case count the days until their server is hijacked and taken offline or permanently destroyed.
    West of House
    You are standing in an open field west of a white house, with a boarded front door.
    There is a small mailbox here.

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