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unable to send to outside recipient with relay on inside server (exchange 2013)

Posted on 2014-09-12
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Last Modified: 2014-09-20
I'm trying to send email to an outside vendor via an intranet server inside my domain. I've created a receive connector on my exchange server using frontend transport and custom type.  Exchange users and anonymous users in the permissions group. Scope is set to the specific web server IP address sending the mail to the relay server. I can send mail to any inside user on exchange.

I added the Get-ReceiveConnector -Identity "Server\RelayConnector" | Add-ADPermission -User "NT AUTHORITY\ANONYMOUS LOGON" -ExtendedRights "ms-Exch-SMTP-Accept-Any-Recipient" at the exchange power shell prompt successfully.  
Still no love. Did I miss a step please?

thanx
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Question by:davebird
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Expert Comment

by:tshearon
ID: 40320252
It doesn't sound like you missed a step. You shouldn't need Exchange Users in your permissions group and I wonder if unticking that would resolve it.
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Author Comment

by:davebird
ID: 40320269
Nope.  That didn't help.  But thank you for the suggestion.
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Expert Comment

by:tshearon
ID: 40320317
Can you provide the error you are receiving?
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Author Comment

by:davebird
ID: 40320322
happy to:  

SERVER -> CLIENT: 220 mail.myserver.com ESMTP Symantec Messaging Gateway
 CLIENT -> SERVER: EHLO web.server.com
 SERVER -> CLIENT: 250-mail.myserver.com says EHLO to 1.2.3.4:14307250-8BITMIME250-ENHANCEDSTATUSCODES250-PIPELINING250 SIZE 10485760
 CLIENT -> SERVER: MAIL FROM:<closed@myserver.com>
 SERVER -> CLIENT: 250 2.0.0 MAIL FROM accepted
 CLIENT -> SERVER: RCPT TO:<david@outsideserver.com>
 SERVER -> CLIENT: 554 5.1.2 Recipient address rejected: User unknown
 SMTP ERROR: RCPT TO command failed: 554 5.1.2 Recipient address rejected: User unknown
 CLIENT -> SERVER: QUIT
 SERVER -> CLIENT: 221 2.3.0 mail.myserver.com closing connection
 SMTP Error: The following recipients failed: david@outsideserver.com
 Mailer Error: SMTP Error: The following recipients failed: david@outsideserver.com
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Expert Comment

by:tshearon
ID: 40320352
Ah so you are using a symantec product as mail proxy or firewall? Is there something you need to change there to allow this? Although I'd suspect you would get an invalid sender message but you never know.
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Author Comment

by:davebird
ID: 40320385
That's an awesome suggestion!  I'll totally check that as a possibility.  My brain is full for tonight but I thank you for your rapid responses.  I'll let you know what I learn (tomorrow).
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Accepted Solution

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davebird earned 0 total points
ID: 40323891
I'm not sure how to say this other than I'm a goober.  Understanding what is happening is a great way to make something work. The connector and the command in PS work if you use the right sending email address to the right server.  
thank you for your responses. Talking through things makes you see what you're staring right at!
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Author Closing Comment

by:davebird
ID: 40334200
I was attempting to authenticate the user from one domain to an open relay on a different domain. Never going to authenticate.  Sorry to have posted but thank you for your efforts.
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