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'Send on Behalf' in Outlook/ Exchange

Posted on 2009-04-18
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Last Modified: 2013-11-30
Hi Experts

I have noticed an interesting phenomenon.

If I send the following command to an Exchange 2003 server;

MAIL FROM: joe_budden@domain.com
RCPT TO: jane_budden@domain.com
DATA
From: Spam@hotmail.com
Subject: Test
Hi, this is a test
.

Then, I will get the following displayed in Outlook:

From: Joe_budden@domain.com on behalf of Spam@hotmail.com

There is NO Sender: header in the email message, so I was curious as to why this 'on behalf of' was added, simply because the MAIL FROM: and From: are different?
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Question by:Joe_Budden
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Expert Comment

by:Mitch1981
ID: 24174977
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Author Comment

by:Joe_Budden
ID: 24174985
Sure - but that is via adding the Sender: header.

In this case, I'm not adding a Sender: header but I still getting 'Send on behalf'?
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Expert Comment

by:Mitch1981
ID: 24175012
"Send on behalf" is not a SMTP command, is a server functionality, you can read the SMTP RFC.

Bye.
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Mestha earned 2000 total points
ID: 24175320
Remember that the From line cannot be relied upon in any shape or form. You could put the from line as bill.gates@microsoft.com and it would be accepted.

What you are have seen is the difference between routing information and display information. The "Mail From" line is used by SMTP to show who the email is from, but this is changed to the simple "From:" in an SMTP client when the headers are built.

I believe the second From: line is how Exchange does the Send on Behalf functionality, which is an Exchange feature that some other clients can work with. For example if you send a Send on Behalf of email between two Exchange servers it will often display correctly with the Send on Behalf of shown.

Basically it is how Outlook has interpreted the double From line.

Simon.
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Author Comment

by:Joe_Budden
ID: 24175502
Excellent, thanks Simon.

Just a query - for applications that send mail, for instance, is the MAIL FROM: derived from the From:. or is the From: usually derived from the MAIL FROM: - or does it completely depend on the app.

For Exchange, I would expect the MAIL FROM: to depend on what the user enters as the From: address in the Outlook client, but how about an application that sends alerts about down servers for instance?
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Expert Comment

by:Mestha
ID: 24179273
It depends on what the sending system sends over during the SMTP communication. All SMTP communication has to take place in a certain order. Once you are past the DATA step in the communication then it comes down to effectively display information and how that it interpreted by the client at the other end.

Simon.
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