Outllok 2010. Pop Account reply to address issue.

Posted on 2011-09-26
Last Modified: 2012-05-12

I'm supporting a user that is a member of a small work group. Windows 7 Pro, with Office 2010 Pro.

The incoming and outgoing server names are correct. The user can send and receive email. But when the recipient of one of his messages attempts to reply, they receive a NDR. In the header of the NDR, it shows the reply to address to be:   username@domainnameCOM , no ".com" (dot com).

I've checked to see if there was a different reply to address in the user account settings in Outlook, but there is none. Other users in the work group are sent up the same as the problem user, and they are operating fine.

Any ideas? Thanks in advance Experts.
Question by:mapalaska2003
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LVL 94

Expert Comment

by:John Hurst
ID: 36639931
Over and above the incoming and outgoing server names, one often has to authenticate the send. Is that necessary here and was that done?

... Thinkpads_User

Author Comment

ID: 36644529
That is how it's configured.
LVL 94

Expert Comment

by:John Hurst
ID: 36646193
Can you give us the headers and key information from a bounce back?

Also, since it is one user, have you checked very thoroughly for malware?  Users sometimes click where they should not. .... Thinkpads_User
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Author Comment

ID: 36711614
User would be the account that is having the issues
User2 is me, the recipient and the one that replied to User.

Hi. This is the qmail-send program at
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

Sorry, I couldn't find any host named domaincom. (#5.1.2)

--- Below this line is a copy of the message.

Return-Path: <User2@domaincom>
Received: (qmail 25455 invoked by uid 10073); 26 Sep 2011 16:37:57 -0800
Received: from by (envelope-from <User2@domaincom>, uid 2020) with qmail-scanner-2.08st
 (clamdscan: 0.96.5/13675. spamassassin: 3.2.5. perlscan: 2.08st.  
 Processed in 1.609441 secs); 27 Sep 2011 00:37:57 -0000
X-Spam-Status: No, hits=-1.2 required=8.0
X-Spam-Report: SA TESTS
  1.2 TO_MALFORMED           To: has a malformed address
  0.0 HTML_MESSAGE           BODY: HTML included in message
 -2.6 BAYES_00               BODY: Bayesian spam probability is 0 to 1%
                             [score: 0.0000]
  0.8 SHORT_HELO_AND_INLINE_IMAGE Short HELO string, with inline image
 -0.6 AWL                    AWL: From: address is in the auto white-list
Received: from (HELO StevensW7PC) (
  by with SMTP; 26 Sep 2011 16:37:55 -0800
From: "User2" <>
To: "'User'" <user@domaincom>
References: <001f01cc7ca4$4fca23b0$ef5e6b10$@user@domaincom>
In-Reply-To: <001f01cc7ca4$4fca23b0$ef5e6b10$@user@domaincom>
Subject: RE: Test 9876
Date: Mon, 26 Sep 2011 16:37:10 -0800
Message-ID: <00aa01cc7cad$97b46470$c71d2d50$@com>
MIME-Version: 1.0
Content-Type: multipart/related;
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: Acx8pEvXQFTqWSl4TESaKpIVMbzWxgACUjAg
Content-Language: en-us

This is a multi-part message in MIME format.

Content-Type: multipart/alternative;

Content-Type: text/plain;
Content-Transfer-Encoding: 7bit

Content-Type: text/html;
Content-Transfer-Encoding: quoted-printable

<html xmlns:v=3D"urn:schemas-microsoft-com:vml" = xmlns:o=3D"urn:schemas-microsoft-com:office:office" = xmlns:w=3D"urn:schemas-microsoft-com:office:word" = xmlns:m=3D"" = xmlns=3D"">

<META HTTP-EQUIV=3D"Content-Type" CONTENT=3D"text/html; = charset=3Dus-ascii"> <meta name=3DGenerator content=3D"Microsoft Word 12 (filtered medium)"> <!--[if !mso]> <style>
v\:* {behavior:url(#default#VML);}
o\:* {behavior:url(#default#VML);}
w\:* {behavior:url(#default#VML);}
.shape {behavior:url(#default#VML);}
 /* Font Definitions */
      {font-family:"Cambria Math";
      panose-1:2 4 5 3 5 4 6 3 2 4;}
      panose-1:2 15 5 2 2 2 4 3 2 4;}
      panose-1:2 11 6 4 3 5 4 4 2 4;}
 /* Style Definitions */
 p.MsoNormal, li.MsoNormal, div.MsoNormal
a:link, span.MsoHyperlink
a:visited, span.MsoHyperlinkFollowed
p.MsoAcetate, li.MsoAcetate, div.MsoAcetate
      mso-style-link:"Balloon Text Char";
      {mso-style-name:"Balloon Text Char";
      mso-style-link:"Balloon Text";
@page Section1
      {size:8.5in 11.0in;
      margin:1.0in 1.0in 1.0in 1.0in;}
<!--[if gte mso 9]><xml>
 <o:shapedefaults v:ext=3D"edit" spidmax=3D"1026" /> </xml><![endif]--><!--[if gte mso 9]><xml>  <o:shapelayout v:ext=3D"edit">
  <o:idmap v:ext=3D"edit" data=3D"1" />

<body lang=3DEN-US link=3Dblue vlink=3Dpurple>

<div class=3DSection1>

<p class=3DMsoNormal><span =

<p class=3DMsoNormal><span =


<div style=3D'border:none;border-top:solid #B5C4DF 1.0pt;padding:3.0pt = 0in 0in 0in'>

<p class=3DMsoNormal><b><span =
style=3D'font-size:10.0pt;font-family:"Tahoma","sans-serif"'> Greg = McClintock [mailto:user@domaincom] <br> <b>Sent:</b> Monday, September 26, 2011 3:31 PM<br> <b>To:</b>; 'User2'<br> <b>Subject:</b> Test 9876<o:p></o:p></span></p>



<p class=3DMsoNormal><o:p>&nbsp;</o:p></p>

<p class=3DMsoNormal><o:p>&nbsp;</o:p></p>

<p class=3DMsoNormal><o:p>&nbsp;</o:p></p>

<p class=3DMsoNormal><b><span style=3D'color:#17365D'>Greg = &quot;Mac&quot; McClintock</span></b><o:p></o:p></p>

<p class=3DMsoNormal><b><i><span =
&amp; Operations Manager</span></i></b><o:p></o:p></p>

<p class=3DMsoNormal><b><span style=3D'font-size:10.0pt'><img =
width=3D119 height=3D67
id=3D"Picture_x0020_1" src=3D"cid:image001.jpg@01CC7C6A.8960C5A0"
alt=3D"GPSAK Email logo"><o:p></o:p></span></b></p>

<p class=3DMsoNormal><b><span style=3D'font-size:10.0pt'>GPS Alaska, = Inc.</span></b><o:p></o:p></p>

<p class=3DMsoNormal><b><span style=3D'font-size:10.0pt'>360 E. = International Airport Rd., Ste10<o:p></o:p></span></b></p>

<p class=3DMsoNormal><b><span style=3D'font-size:10.0pt'>Anchorage, = Alaska&nbsp; 99518</span></b><o:p></o:p></p>

<p class=3DMsoNormal><b>907.562.8000</b><o:p></o:p></p>

<p class=3DMsoNormal><b>Fax: 907.562.8080</b><o:p></o:p></p>

<p class=3DMsoNormal><o:p></o:p></p>

<p class=3DMsoNormal><o:p></o:p></p>

<p class=3DMsoNormal><span =

<p class=3DMsoNormal><span style=3D'font-size:10.0pt'><img width=3D162 =
id=3D"Picture_x0020_2" src=3D"cid:image002.png@01CC7C6A.8960C5A0"

LVL 94

Expert Comment

by:John Hurst
ID: 36711648
That email error (for me 100% of the time) means the wrong email address was used.

.... Thinkpads_User

Author Comment

ID: 36711757
The wrong email address from where? I'm trying to figure that out.
LVL 94

Expert Comment

by:John Hurst
ID: 36711789
Your Outlook sends an email out with addresses, so somehow, the address has been incorrectly formed.

Send the same email to the same person (address not found) and copy a friend. Then look at the friend's email to see if you can sort out what the error is. ... Thinkpads_User

Author Comment

ID: 36711817
I'm having the user send me a fresh (not forwarded) message. I'll look in the header info for clues as to where the return address is incorrectly formed. I'll reply and cc myself and look at that header info too. I'll let you kno=w what I come up with. I sure apreciate your help. This is not the first time you have helped me out.

Author Comment

ID: 36712161
Looking at the header information, from a fresh email from the user to me, it shows that the reply address is clearly where the problem appears to be. In Outlook, no alternate reply address was specified. I did try to specify the correct reply to address yesterday, in Outlook", bt it made no difference.

Received: (qmail 20592 invoked by uid 10073); 27 Sep 2011 10:32:11 -0800
Received: from by (envelope-from <user@domaincom>, uid 2020) with qmail-scanner-2.08st
 (clamdscan: 0.96.5/13680. spamassassin: 3.2.5. perlscan: 2.08st.  
 Processed in 1.46726 secs); 27 Sep 2011 18:32:10 -0000
X-Spam-Status: No, hits=4.2 required=8.0
X-Spam-Level: ++++
X-Spam-Report: SA TESTS
  2.7 FH_FROMEML_NOTLD       E-mail address doesn't have TLD (.com, etc.)
  1.9 TVD_RCVD_IP            TVD_RCVD_IP
  1.4 MSGID_MULTIPLE_AT      Message-ID contains multiple '@' characters
  0.0 HTML_MESSAGE           BODY: HTML included in message
 -2.6 BAYES_00               BODY: Bayesian spam probability is 0 to 1%
                             [score: 0.0000]
  0.8 SHORT_HELO_AND_INLINE_IMAGE Short HELO string, with inline image
 -0.1 AWL                    AWL: From: address is in the auto white-list
X-Qmail-Scanner-Mail-From: user@domaincom via
X-Qmail-Scanner: 2.08st (Clear:RC:0( Processed in 1.46726 secs Process 20569)
Received: from (HELO JDHJ6K1GAK) (
  by with SMTP; 27 Sep 2011 10:32:08 -0800
From: "USER NAME" <user@domaincom>
Subject: Fresh Email
Date: Tue, 27 Sep 2011 10:32:11 -0800
Message-ID: <000001cc7d43$c63a6ba0$52af42e0$@user@domaincom>
MIME-Version: 1.0
Content-Type: multipart/related;
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: Acx9Q8SG9T/oMaVkQ/iaO77ImTYr+g==
Content-Language: en-us

LVL 94

Accepted Solution

John Hurst earned 500 total points
ID: 36712198
If the address here is a contact, please delete the contact (you can always remake it). Then in Outlook, go to Options -> Accounts and edit the email account you are using. Eliminate the "Reply to" Address in there and just have your own email address and name in the Change Account screen in the first two setup lines.

So: no contact, no reply address. Now try sending a test email by typing in the complete address (no recent or cached address). If you get an error, post it here. ... Thinkpads_User

Author Closing Comment

ID: 36957528
LVL 94

Expert Comment

by:John Hurst
ID: 36957536
You are most welcome and I was pleased to assist. ... Thinkpads_User

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