My_Server.*********.local rejected your message to the following e-mail addresses

Posted on 2012-08-11
Last Modified: 2012-08-15
Every time I try to send am e-mail from a client PC to a certain e-mail address running on my exchange server (MS Exchange 2010 Entrprs) I get the following rejection message.... Any help please to work it out?

Thank you,

Rejection message that I get:

My_Server.*********.local rejected your message to the following e-mail addresses:
My_Server.*********.local gave this error:
Client was not authenticated
Your message wasn't delivered due to a permission or security issue. It may have been rejected by a moderator, the address may only accept e-mail from certain senders, or another restriction may be preventing delivery.

Diagnostic information for administrators:
Generating server: My_Server.*********.local
My_Server.*********.local #530 5.7.1 Client was not authenticated ##
Original message headers:
Received: from ChrysanthyPC ( by mail.*********.com
 ( with Microsoft SMTP Server id 14.1.****.1; Sat, 11 Aug 2012
 18:40:33 +0300
Return-Receipt-To: Chrysanthy ********<chrys@*********.com>
From: Chrysanthy ********<chrys@********.com>
To: <Chrys@***22222*******.com>
Subject: 777
Date: Sat, 11 Aug 2012 17:40:35 +0300
MIME-Version: 1.0
Content-Type: multipart/related;
X-Priority: 1 (Highest)
X-MSMail-Priority: High
X-Mailer: Microsoft Office Outlook 12.0
Importance: High
Thread-Index: Ac13zzIXyY4rG7rnSIWcTA87bIHvLw==
Content-Language: en-us
Disposition-Notification-To: Chrysanthy *******<chrys@*******.com>
Return-Path: chrys@********.com
Question by:Dr.Costas Sachpazis
    LVL 39

    Assisted Solution

    Can you give more details?
    1. What mail client is used and why smtp authorization is not used.
    2. Is sender address in same domain as recipient? Very often for blocking spam messages inside domain required authorization.
    3. Is anonymous mail receipt allowed?
    Try to make tests with telnet. May be you can find reason. Tests you can find here:

    Author Comment

    by:Dr.Costas Sachpazis
    Thank you!

    I will follow your suggestion and come back with feedback.
    LVL 6

    Assisted Solution

    It's also possible that the person you are sending to has a really strict spam filter.  It may be your fault, but don't discount them having rules preventing you from emailing them unless they have you on a safe list.
    LVL 52

    Assisted Solution

    Is there a "Accepted Domain" for "********.com" ??
    Can the internal user send email to internal user ?
    Can the internal user send email to external user ?

    Is "Anonymous Users" option selected on the "Receive connector" ??
    Is the Transport and other MS services running on the server ??

    Is there a MX record with ISP for your Servers so they can receive emails from Internet ? and is port 25 open ?

    - Rancy
    LVL 76

    Accepted Solution

    Your organization seems to have multiple segments make sure that your exchange relay rules allows segment to send through.

    This might be a VPN segment. Because the is not explicitly allowed to relay through the exchange server, you can avoid this issue by configuring your outlook mail client to always authenticate to send smtp messages.  This way no matter how you connect to the exchange server, you will always be permitted to send through it.

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