Exchange 2010 : My Email does not send to a external address

Jake Ives
Jake Ives used Ask the Experts™
Having an issue with Exchange 2010.

I'm trying to send an email to an external recipient but when sending I instantly get the below bounceback.

This only happens to one address, sending email to any other address is fine.

I've changed the emails in the bounceback below to fictitious emails.

Requested rejected your message to the following e-mail addresses: (
Requested gave this error:
Transaction failed
A problem occurred during the delivery of this message to this e-mail address. Try sending this message again. If the problem continues, please contact your helpdesk.

Diagnostic information for administrators:
Generating server: COMPANY-EX-01.MyServer.local
Requested #554 Transaction failed ##
Original message headers:
Received: from COMPANY-EX-01.MyServer.local ([fe80::9cff:7ac1:270a:6af8])
 by COMPANY-EX-01.MyServer.local ([fe80::9cff:7ac1:270a:6af8%10]) with mapi
 id 14.03.0319.002; Thu, 23 Mar 2017 17:02:59 +0000
From: Jake Ives <>
To: "" <>
Thread-Topic: Delivery to EMAIL SUBJECT
Thread-Index: AdKi/tBvzSBmo8UoS3q0O4COzZS2BgA8xargAAFL4OAAAAvN4A==
Date: Thu, 23 Mar 2017 17:02:58 +0000
Message-ID: <5FECE51540A5FC44B6071565BC4C3D33447C967F@COMPANY-EX-01.MyServer.local>
References: <5FECE51540A5FC44B6071565BC4C3D33447C7BD8@COMPANY-EX-01.MyServer.local>
In-Reply-To: <5FECE51540A5FC44B6071565BC4C3D33447C9654@COMPANY-EX-01.MyServer.local>
Accept-Language: en-US, en-GB
Content-Language: en-US
X-MS-Has-Attach: yes
x-originating-ip: []
Content-Type: multipart/mixed;
MIME-Version: 1.0
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Error 554 indicates that the recipient's server is either rejecting the sender, or the sender's email domain.

Maybe reach out to them and ask to be whitelisted
Jake IvesSenior Engineer


But the generating server is COMPANY-EX-01.MyServer.local (My Server) and not the external server - The bounceback is sent extremely fast (Almost as if to suggest it hasn't even left the exchange server)
try going to and run their domain thru there diagnostics to see if anything turns up and if so post back the results.
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Tim EdwardsIT Team Lead - Unified Communications & Collaboration
Any rules, spam filters that could be blocking the message? What happens if just send a generic email that would have no virus, spam, marketing ratings that could be blocked.
Jake IvesSenior Engineer


Hi Tim,

I have tried sending an email with just 'test' in the body. Still bounces back!
Tim EdwardsIT Team Lead - Unified Communications & Collaboration

As per above I would look a mxtoolbox and contact the recipient to see if they have the user blacklisted.

Have you attempted to send to this email from another user as well and did it go out? Are you going directly out to the internet or are you going through and edge server or spamfirewall?
MASEE Solution Guide - Technical Dept Head
Most Valuable Expert 2017

No comment has been added to this question in more than 21 days, so it is now classified as abandoned.

I have recommended this question be closed as follows:

-- Kaffiend (https:#a42062082)
-- Tim Edwards (https:#a42062128)

If you feel this question should be closed differently, post an objection and the moderators will review all objections and close it as they feel fit. If no one objects, this question will be closed automatically the way described above.

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