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Exchange doesn't bounce to same sender address

Posted on 2009-05-20
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Last Modified: 2012-05-07
HI. I bounce my work email to a Gmail account, as a backup. This is set up to forward to the gmail contact from Exchange. Exchange on Server 2003.

However, I've noticed that when I email my work account from the gmail account, I don't receive a copy of it to my gmail afterwards.

Anything coming to my work email should automatically end up in my gmail, but if an email is sent from the account itself, Exchange doesn't forward...

Is there any setting I can change so that Exchange will forward everything, even if it originates from the account which it is forwarding to?
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Question by:mharcais
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11 Comments
 
LVL 15

Expert Comment

by:abhaigh
ID: 24430543
you would need to configure a rule that fires on sending within Outlook

From what I see this would be of the form of

Apply this rule asfter I send a message
Cc the message to "people or distribution list"

replacing "people or distribution list" with your external contact details
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Author Comment

by:mharcais
ID: 24430995
HI, just to clarify - this forwarding is not done at Outlook level, it is done from within Exchange...
As soon as an email arrives at Exchange it is bounced, before it reaches the users inbox...
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LVL 15

Expert Comment

by:abhaigh
ID: 24431065
Yes, any and all email sent into Exchange *to* that account will be forwarded out to your external mailbox

However, the only way you are going to get a copy of everything you send *from* that account forwarded to your external mailbox will have to be dealt with at the client level. Exchange does not possess that functionality
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LVL 32

Expert Comment

by:gupnit
ID: 24431340
Hi,
When you set up forwwarding at server level, in that case this is the default behaviour. Even if you send mail from any yahoo/hotmail or any external domains, you would not be receiving mails to external ID (as forwarded). Please test.
Outlook Rules are one way of doing it, provided Forwarding is allowed at Global LEvel on your servers, as a best practice it is disabled
Let me know
Thanks
Nitin Gupta (gupnit)
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Author Comment

by:mharcais
ID: 24432313
Hi, I have the forwarding set through Active Directory already.

Active Directory > Users > Me > Exchange General > Delivery Options > Forwarding Address > (Deliver message to both forwarding address and mailbox)

It works perfectly for all mail I receive: everything gets bounced to the gmail account I have specified in the tab above...

EXCEPT if I send an email from the actual Gmail account back to my work email.

It arrives into my work email, but never gets bounced on to the Gmail....
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LVL 32

Expert Comment

by:gupnit
ID: 24432443
Hi,
Can you try sending from some other domain like Yahoo and see if mail gets diverted to Gmail. I would doubt that, please confirm, so that I can guide further
Thanks
Nitin
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LVL 65

Accepted Solution

by:
Mestha earned 2000 total points
ID: 24432631
Message tracking will show whether the message is forward or not. It is probably Google's antispam functionality. When a message passes through Exchange on automatic forwarding it can look like spoofing. If the recipient envelope and the From line are the same, then that would look like spam, particularly as the message is not coming from a Google IP address.

Simon.
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Author Comment

by:mharcais
ID: 24433309
HI - yes, every single email that is sent to my work email from a wide variety of external domains DO certainly end up at the gmail account.

It is only emails sent from the gmail account to the work account that never get bounced on...
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Author Comment

by:mharcais
ID: 24473230
yahoo > work email
                     >>> Arrives in work email, plus
                     >>> Forwards copy to Work Gmail

Hotmail > work email
                     >>> Arrives in work email, plus
                     >>> Forwards copy to Work Gmail

Work Gmail > Work email
                     >>> Arrives in work email, but
                     >>> DOES NOT forward to Work Gmail
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LVL 65

Expert Comment

by:Mestha
ID: 24475344
What you see in the account doesn't prove anything.
As I have said in a previous response you need to look at message tracking to see if Exchange is sending the message out. If it is then there is nothing you can do about it.

Simon.
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LVL 15

Expert Comment

by:abhaigh
ID: 24478964
I did some testing today with the same setup and got he same results. I'm thinking that gmail is seeingthe mail come in with an originating addess the same as the destination address and is probably dropping it quietly as it thinks that the email is spam as Mestha has already suggested.

as it is, aren't you keeping a copy of all outbound gmail in your sent items folder there anyway?
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