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Can't send out spoofed mail

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Can't send out spoofed mail - 7.May2008 4:40:43 AM   
pb1

 

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I need to be able to send out spoofed mails..

We have a system that send out mail to one of our customers.. and the from field in the mail should be a mail from our custommers domain.. the reason is that people reply on the mail and the customer wants the reply back to there exchange server...

I keep getting the error: smtp;550 5.7.1 This system is configured to reject spoofed sender addresses
 
I can send mail to x@gmail.com from exchange as x@MyCustomer.com
I can send mail to my exchange from exchange as x@MyCustomer.com
 
But I can't send mail to my Customer as x@MyCustomer.com !! The mail is not rejected by there server! I have used message tracking and the mail never exit our Exchange server! My exchange wont' send it out!?!
 
I have tried telnet to my customers mail server... as soon as i type.
mail from: x@MyCustomer.com
 
I get: smtp;550 5.7.1 This system is configured to reject spoofed sender addresses
Post #: 1
RE: Can't send out spoofed mail - 7.May2008 9:33:33 AM   
uemurad

 

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quote:

I have tried telnet to my customers mail server... as soon as i type.
mail from:
x@MyCustomer.com

 
I get: smtp;550 5.7.1 This system is configured to reject spoofed sender addresses
Since you are telnetted to your customer's server, then the response is coming from that server.  Whatever is fielding SMTP messages on that server (whether it's Exchange or some other SMTP engine) is rejecting the spoofed address.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to pb1)
Post #: 2
RE: Can't send out spoofed mail - 7.May2008 10:18:48 AM   
pb1

 

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This is the message tracking event for that mail






(in reply to uemurad)
Post #: 3
RE: Can't send out spoofed mail - 7.May2008 10:52:45 AM   
uemurad

 

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Joined: 7.Jan.2004
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What you saw from your telnet session is what your Exchange server sees when communicating with the customer system.  Their system doesn't send back a fully-formed NDR, but instead returns a non-OK code (5.7.1).  Your Exchange server then interprets the code and generates a message to help you understand what has happened.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to pb1)
Post #: 4
RE: Can't send out spoofed mail - 7.May2008 2:55:50 PM   
pb1

 

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Joined: 19.Mar.2008
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Okay..
I have another mail server (not exchange) I have no problem sending spoofed mail from that server.. I'm using that server atm, but I want to kill that server so I need it to work on exchange.

Just seems strange that my customer should accept from my old non exchange server!?

thanks for your help so far :)

(in reply to uemurad)
Post #: 5
RE: Can't send out spoofed mail - 7.May2008 4:31:49 PM   
uemurad

 

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Joined: 7.Jan.2004
From: California, USA
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Since their system disallows your Exchange server to spoof, yet allows your old server to do so, it seems logical to assume that it's configurable on some level.  Perhaps by IP address?

You said in your original post that you didn't think their system was rejecting the messages.  Was that what you were told, or was that your conclusion based on your analysis?

What happens if you perform the telnet test from that system?  Compare all the SMTP commands and responses from your two systems.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to pb1)
Post #: 6
RE: Can't send out spoofed mail - 8.May2008 5:43:21 AM   
pb1

 

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Joined: 19.Mar.2008
Status: offline
It's based on my analysis..

tried to telnet from my other server.. and also getting :
This system is configured to reject spoofed sender addresses

but they are geeting the mails!?!?!



(in reply to uemurad)
Post #: 7
RE: Can't send out spoofed mail - 8.May2008 9:13:23 AM   
uemurad

 

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Joined: 7.Jan.2004
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I don't know what else to tell you.  It is their configuration that is blocking the messages from getting through.  When you connect to their system with telnet, does their system identify itself as a Microsoft ESMTP server?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to pb1)
Post #: 8

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