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Why mails turned to bad mails using smtp relay?

Posted on 2014-02-12
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Last Modified: 2014-02-26
This is using w2k8 r2 iis smtp relay to use office 365 mail server. There are few printers, 1 navisions server, and 1 application using bugzilla, all pointing to this smtp relay for sending mails.

On smtp relay, it was configured with smtp port 587 with tls, and using one admin account - administrator. I did a quick test :

   - telnet smtp_ip 25
  - helo
  - mail from: administrator@abc.com
  - rcpt to: user@otherdomain.com
  - data
  - this is a clear test
  .
  - quit

 Mail can sent out no problem. The problem is on this bugzilla appln, in which mail ended as bad mail. The error message is: 550 5.7.1 clint do not have permissions to send as its sender.

What is the problem?

Thsnks
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Question by:MichaelBalack
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6 Comments
 
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Author Comment

by:MichaelBalack
ID: 39855057
Hi all,

On bugzilla appln, please see few settings on mailing:

  From: bugzilla@abc.com
  Smtp: smtp_ip

On iis smtp relay:

  Clear text authentication: administrator@abc.com
   Password: password
   Allow whole office network for connection and relay.

The office 365 account - administrator, has a primary mailbox named administrator@abc.com, plus bugzilla@abc.com as well.
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Expert Comment

by:Vasil Michev (MVP)
ID: 39855420
So bugzilla@abc.com and administrator@abc.com are two different mailboxes? If this is the case, have you granted the necessary Send As/Send on behalf permissions?
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Author Comment

by:MichaelBalack
ID: 39855538
Bugzilla@ and administrator@ are the same mailbox belong to administrator.
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Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 39861044
You shouldn't need to run the email from Bugzilla through your relay -- because Bugzilla has the ability to send TLS by itself.

Jeff
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Accepted Solution

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Jeffrey Kane - TechSoEasy earned 500 total points
ID: 39861052
But... if you still want to, then you need to configure your RELAY server's permissions.  Just because Office365 knows that its okay for bugzilla@ to send mail on behalf of administrator@, your Relay Server doesn't know and it's getting confused.

See http://www.o365info.com/2013/01/smtp-relay-in-office-365-environment.html for details on this.
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Author Closing Comment

by:MichaelBalack
ID: 39891172
It works
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