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

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

tshearon

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.

David Bird

ASKER

Nope. That didn't help. But thank you for the suggestion.

tshearon

Can you provide the error you are receiving?

David Bird

ASKER

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

tshearon

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.

David Bird

ASKER

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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David Bird

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David Bird

ASKER

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.