Solved

Message not delivered to hotmail.

Posted on 2007-04-04
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1,524 Views
Last Modified: 2013-12-09
The following message is not successfully delivered to hotmail. It doesn't even make it into the junk folder. I have also tried adding the address to the whitelist and still no luck. This was a test message sent to gmail:

                                                                                                                                                                                                                                                               
Delivered-To: kapmail@gmail.com
Received: by 10.114.192.10 with SMTP id p10cs22086waf;
        Mon, 2 Apr 2007 23:23:37 -0700 (PDT)
Received: by 10.35.70.2 with SMTP id x2mr10750669pyk.1175581416909;
        Mon, 02 Apr 2007 23:23:36 -0700 (PDT)
Return-Path: <service@tnbdistribution.com>
Received: from tnbdistribution.com (thenaughtybag.com [70.86.4.34])
        by mx.google.com with ESMTP id w38si10789399pyg.2007.04.02.23.23.36;
        Mon, 02 Apr 2007 23:23:36 -0700 (PDT)
Received-SPF: pass (google.com: domain of service@tnbdistribution.com designates 70.86.4.34 as permitted sender)
Received: (qmail 10773 invoked from network); 2 Apr 2007 23:23:16 -0700
Received: from tnbco.com (HELO tnbdistribution.com) (70.86.4.36)
  by tnbco.com with SMTP; 2 Apr 2007 23:23:16 -0700
MIME-Version: 1.0
From: "Damien Taylor" <service@tnbdistribution.com>
Subject: Your conversation has been updated
Date: Mon,  2 Apr 2007 23:23:16 -0700
Content-Type: multipart/related;
      boundary="=_f2d1a987bcc34f195cca17b0da02d715"
Message-ID: <jfwses.giuvcc@tnbdistribution.com>
To: "Christopher Mouton" <kapmail@gmail.com>

--=_f2d1a987bcc34f195cca17b0da02d715
Content-Type: text/html; charset="ISO-8859-1"
Content-Transfer-Encoding: quoted-printable

<html><head><style type=3D"text/css">
      .Footer {
            font-family:verdana, arial, sans-serif;
            font-size:10px;
            color:#666666;
            padding:0 16px 8px 16px;
            text-align:center;
      }
      .Footer a{
            font-family:verdana, arial, sans-serif;
            font-size:10px;
            color:#666666;
            text-decoration:none;
      }
      .Footer a:hover{
            text-decoration:underline;
      }
      </style>
      </head>
      <body background=3D"cid:b240ee56fbd5777acc03b0863d6196b4">
      <table width=3D"100%"><tr><td align=3D"center">
      <div style=3D"width:500px;">
            <div style=3D"border-width:1px; border-style:solid; border-color:#000; ba=
ckground-color:#FFF; text-align:left;">
                  <img style=3D"margin:2px 0 25px 116px;" src=3D"cid:1f8b8aae07e0bd6942f0b=
3318521fc11" alt=3D"" width=3D"265" height=3D"52" />
                  <div style=3D"font-family:verdana, arial, sans-serif; font-size:16px; co=
lor:#7F7F7F; font-weight:bold; text-align:center; margin-bottom:26px;">Your=
 <span style=3D"color:#990000">conversation</span> has been updated!</div>
                  <div style=3D"font-family:verdana, arial, sans-serif; font-size:12px; co=
lor:#333; padding:0 16px 16px 16px;"><b>The conversation you initiated has =
been updated on the customer service area</b><div><br /></div><a href=3D"ht=
tp://tnbdistribution.com/s/support/contact.php?TID=3D16&CS=3D2504860571">ht=
tp://tnbdistribution.com/s/support/contact.php?TID=3D16&CS=3D2504860571</a>
                        <div><br /></div>
                        To protect your privacy, the response will be available when you login =
to your account. If you have further questions or a comment you will be abl=
e to continue the conversation.
                        <div><br /></div>
                        Replies to this email cannot be read, but I look forward to continuing =
our conversation online.<div style=3D"text-align:right; margin-top:40px;"><=
table style=3D"font-family:verdana, arial, sans-serif; font-size:12px; colo=
r:#333333; border-width:0; padding:0; margin:0;"><tr><td>Sincerely,<br />Da=
mien Taylor<br />Chief Marketing Officer</td></tr></table></div>
                  </div>
                  <div class=3D"Footer" style=3D"font-family:verdana, arial, sans-serif; f=
ont-size:10px; color:#666; padding:0 16px 8px 16px; text-align:center;"><a =
href=3D"http://tnbdistribution.com/n/bag/bag.php">Edit my bag<sub>&reg;</su=
b></a> | <a href=3D"http://tnbdistribution.com/n/bag/account.php">Edit my a=
ccount</a> | <a href=3D"http://tnbdistribution.com/n/bag/account.php">Manag=
e email preferences</a>
                        <br />&copy; 2007 TNB Distribution, LLC | 4580 S. Valley View Blvd. B-2=
 | Las Vegas, NV | 89103
                  </div>
            </div>
      </div>
      </td></tr></table></body></html>
--=_f2d1a987bcc34f195cca17b0da02d715
Content-Type: image/gif
Content-Transfer-Encoding: base64
Content-Disposition: inline; filename="email_background.gif"
Content-ID: <b240ee56fbd5777acc03b0863d6196b4>

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--=_f2d1a987bcc34f195cca17b0da02d715
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Content-ID: <1f8b8aae07e0bd6942f0b3318521fc11>

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--=_f2d1a987bcc34f195cca17b0da02d715--
0
Comment
Question by:sypder
  • 19
  • 8
  • 8
35 Comments
 
LVL 36

Expert Comment

by:grblades
ID: 18852010
> Received: from tnbdistribution.com (thenaughtybag.com [70.86.4.34])

This is not quite right. You should update the reverse DNS (PTR record) for 70.86.4.34 to point to tnbdistribution.com. instead of thenaughtybag.com.
0
 
LVL 3

Author Comment

by:sypder
ID: 18852027
Hmmm... My server has multiple IP address, 70.86.4.34 is thenaughtybag.com and 70.86.4.36 is tnbdistribution.com.

I am not sure if there is a way to get it go out on 36 and not 34.

The email also has Received: from tnbco.com (HELO tnbdistribution.com) (70.86.4.36)
0
 
LVL 36

Expert Comment

by:grblades
ID: 18852086
Multiple IP addresses is not a problem when receiving email.
When sending it will always tend to use one IP address and you just need to make sure that whatever the server uses in its HELO command is the same as what is retrieved when doing a reverse loopup on the IP address and a DNS lookup on the domain also matches its IP address.
0
 
LVL 3

Author Comment

by:sypder
ID: 18852304
Does this look better then:

Delivered-To: kapmail@gmail.com
Received: by 10.114.192.10 with SMTP id p10cs218768waf;
        Wed, 4 Apr 2007 10:45:07 -0700 (PDT)
Received: by 10.90.79.6 with SMTP id c6mr832417agb.1175708707089;
        Wed, 04 Apr 2007 10:45:07 -0700 (PDT)
Return-Path: <service@tnbdistribution.com>
Received: from tnbdistribution.com (thenaughtybag.com [70.86.4.34])
        by mx.google.com with ESMTP id 10si3609558nzo.2007.04.04.10.45.00;
        Wed, 04 Apr 2007 10:45:06 -0700 (PDT)
Received-SPF: pass (google.com: domain of service@tnbdistribution.com designates 70.86.4.34 as permitted sender)
Received: (qmail 19285 invoked from network); 4 Apr 2007 10:44:54 -0700
Received: from tnbco.com (HELO thenaughtybag.com) (70.86.4.36)
  by tnbco.com with SMTP; 4 Apr 2007 10:44:54 -0700
MIME-Version: 1.0
From: "Damien Taylor" <service@tnbdistribution.com>
Subject: Your conversation has been updated
Date: Wed,  4 Apr 2007 10:44:54 -0700
Content-Type: multipart/related;
      boundary="=_60a6682a557a551d90e104bcb12f0cde"
Message-ID: <jfzimu.u2eox6@tnbdistribution.com>
To: "Christopher Mouton" <kapmail@gmail.com>
0
 
LVL 36

Expert Comment

by:grblades
ID: 18852344
Not quite. It looks the same to me. I think if you changed the PTR record it will be fine but of course it can take a few hours to take effect.

Received: from tnbdistribution.com (thenaughtybag.com [70.86.4.34])


0
 
LVL 3

Author Comment

by:sypder
ID: 18852406
Okay, so we are talking about this line:

Received: from tnbdistribution.com (thenaughtybag.com [70.86.4.34])

and not:

Received: from tnbco.com (HELO thenaughtybag.com) (70.86.4.36)

So the first line should read: Received: from thenaughtybag.com (thenaughtybag.com [70.86.4.34])?
0
 
LVL 3

Author Comment

by:sypder
ID: 18852421
So how does this look:

Delivered-To: kapmail@gmail.com
Received: by 10.114.192.10 with SMTP id p10cs220911waf;
        Wed, 4 Apr 2007 11:03:12 -0700 (PDT)
Received: by 10.90.69.8 with SMTP id r8mr878828aga.1175709791705;
        Wed, 04 Apr 2007 11:03:11 -0700 (PDT)
Return-Path: <service@tnbdistribution.com>
Received: from thenaughtybag.com (thenaughtybag.com [70.86.4.34])
        by mx.google.com with ESMTP id n45si1323812pyh.2007.04.04.11.03.11;
        Wed, 04 Apr 2007 11:03:11 -0700 (PDT)
Received-SPF: pass (google.com: domain of service@tnbdistribution.com designates 70.86.4.34 as permitted sender)
Received: (qmail 20549 invoked from network); 4 Apr 2007 11:03:06 -0700
Received: from tnbco.com (70.86.4.36)
  by tnbco.com with SMTP; 4 Apr 2007 11:03:06 -0700
MIME-Version: 1.0
From: "Damien Taylor" <service@tnbdistribution.com>
Subject: Your conversation has been updated
Date: Wed,  4 Apr 2007 11:03:05 -0700
Content-Type: multipart/related;
      boundary="=_fd247cde117358108f53a25ad246040b"
Message-ID: <jfzjh5.vsfedm@tnbdistribution.com>
To: "Christopher Mouton" <kapmail@gmail.com>
0
 
LVL 36

Expert Comment

by:grblades
ID: 18852960
That looks fine. Thats the server which is connecting to google, hotmail etc... so it is the one checked by them.
0
 
LVL 3

Author Comment

by:sypder
ID: 18854319
I am still trying to send to Hotmail and it just doesn't make it through. I have no idea what. I also signed up for Smart Network Data Services and I don't see any traffic. What else can I try.

I also submitted the SPF cache to MSN, and no change after that.
0
 
LVL 36

Expert Comment

by:grblades
ID: 18856607
Sorry I cannot see any other reason why they would be blocking the emails.

I have found this link http://www.freshmango.com/articles/display/?articleID=24 which also points to a few other threads with people discussing the same problem you are having.
0
 
LVL 32

Expert Comment

by:r-k
ID: 18862391
Try sending a test mail (while logged in on the server) with telnet.

Examples here:

http://support.microsoft.com/default.aspx?scid=kb;en-us;153119
http://www.yuki-onna.co.uk/email/smtp.html
0
 
LVL 3

Author Comment

by:sypder
ID: 18867674
r-k, you might be on to something. I tried this and I got this error:

553 sorry, that domain isn't in my list of allowed rcpthost
0
 
LVL 3

Author Comment

by:sypder
ID: 18867681
I am still getting the 553 sorry, that domain isn't in my list of allowed rcpthost, but that is for all domains, email address that I can send emails to.

I am SSHing in on port 22 for my server, then telneting into port 25 and 'HELO localhost'
0
 
LVL 36

Expert Comment

by:grblades
ID: 18867719
You should do 'HELO thenaughtybag.com' as that is the name of your server and is what it advertises its name as.
0
 
LVL 3

Author Comment

by:sypder
ID: 18867731
After telneting in I issued the command auth login and then entered my base64 username and password.
0
 
LVL 32

Expert Comment

by:r-k
ID: 18867733
I think you should use the correct name for your domain in HELO
e.g. HELO mydomain.com

(assuming your return address is you@mydomain.com)

You can try first with a domain where you are able to send mails, normally, just to be sure of success.

0
 
LVL 36

Expert Comment

by:grblades
ID: 18867741
You telneted to hotmails server and not your own correct?
0
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LVL 3

Author Comment

by:sypder
ID: 18867745
Okay, I have it working, and when I send to my hotmail address it returns:

MAIL FROM: service@tnbNOSPAMdistribution.com
250 ok                                
RCPT TO: chris22ca@hotNOSPAMmail.com        
250 ok                                
DATA                                  
354 go ahead                          
Subject: testing to hotmail          
This is a test using telnet directly.
.                                    
250 ok 1175895744 qp 8185            
0
 
LVL 3

Author Comment

by:sypder
ID: 18867747
grblades: Oh... I must be misunderstanding what I am trying to do. I am suppose to telnet to Hotmails server?
0
 
LVL 32

Expert Comment

by:r-k
ID: 18867770
Yes, you first want to log-in on your server.

Then, from your server, you want to telnet to port 25 on the hotmail server (you could try mx1.hotmail.com)
etc.

If you want to test with Yahoo for comparison, their mail server is ns1.yahoo.com

0
 
LVL 3

Author Comment

by:sypder
ID: 18867792
Thanks. I telneted to mx1.hotmail.com 25 from my server and here is what the server returned when I sent a test message:

250 <BAY0-MC2-F3fRS8Lbyi0009e22e@bay0-mc2-f3.bay0.hotmail.com> Queued mail for d
elivery                                                                        
0
 
LVL 36

Assisted Solution

by:grblades
grblades earned 200 total points
ID: 18867798
In addition you should also ideally be using the EHLO command instead of HELO as that is what practically all mail servers use now to indicate they support enhanced SMTP. The sender then gives additional messages about the email intending to be sent such as its size which allows the receiving server to reject the mail early or give additional error messages.

Sorry I dont have an example of EHLO in use and I am off to sleep shortly.
0
 
LVL 3

Author Comment

by:sypder
ID: 18867806
qrblades: I did actually use EHLO, the example from Microsoft used that, so that is what I used.
0
 
LVL 32

Expert Comment

by:r-k
ID: 18867813
Looks like hotmail accepted mail from your server. If you sent it your own account at hotmail you can now see if it arrives shortly.

For comparison you may want to send (with telnet) to another server where you have an account to see if there is any difference.
0
 
LVL 3

Author Comment

by:sypder
ID: 18867816
EHLO thenaughtybag.com                                                
250-bay0-mc10-f7.bay0.hotmail.com (3.3.2.16) Hello [70.86.4.34]        
250-SIZE 29696000                                                      
250-PIPELINING                                                        
250-8bitmime                                                          
250-BINARYMIME                                                        
250-CHUNKING                                                          
250-AUTH LOGIN                                                        
250-AUTH=LOGIN                                                        
250 OK                                                                
MAIL FROM: service@tnbdistribution.com                                
250 service@tnbdistribution.com....Sender OK                          
RCPT TO: chris22ca@hotmail.com                                        
250 chris22ca@hotmail.com                                              
DATA                                                                  
354 Start mail input; end with <CRLF>.<CRLF>                        
Subject: A test subject                                                        
This is my test body                                                          
.                                                                              
250 <BAY0-MC10-F7oMCeV9f000736ff@bay0-mc10-f7.bay0.hotmail.com> Queued mail for delivery            
Connection closed by foreign host.                                                              
0
 
LVL 3

Author Comment

by:sypder
ID: 18867820
r-k: It is still not in my hotmail account, and I even have the from address in my whitelist.
0
 
LVL 32

Expert Comment

by:r-k
ID: 18867834
Is "thenaughtybag.com" your real domain?

I would not be surprised if Hotmail blocks (i.e. silently deletes) everything with the word "naughty" in the address....

Or it could just be that their server is slow right now.

Check your hotmail bulk folder just in case.
0
 
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Author Comment

by:sypder
ID: 18867844
Yeah, thenaughtybag.com is the real address, the company name is TNB Distribution, LLC. The TNB is for "The Naughty Bag."

Nothing in my bulk folders, and I have been doing these sorts of tests for days, and still nothing. If I do the same thing, but from my personal address, it goes right through. I have read some people say the "Queued mail for delivery" is a sign that they have flagged it as spam.
0
 
LVL 3

Author Comment

by:sypder
ID: 18867847
I can rename the server and switch the IPs for tnbdsitribution.com and thenaughtybag.com.

Do others think that this could resonably be the problem?
0
 
LVL 32

Expert Comment

by:r-k
ID: 18867866
As a comparison, I just used telnet to mx1.hotmail.com and sent myself a short message (following what you posted above pretty closely except using my own domain) and got exactly the same response that you posted above.

The big difference is that in my case the message arrived at my hotmail accnt within 30 secs.

So I think that makes it very likely that hotmail is filtering on words in the address field. I don't think they should, either, but some ISP's are going too far in their effort to control spam.
0
 
LVL 3

Author Comment

by:sypder
ID: 18867872
I am going to switch up the IPs so that everything is based on tnbdistributoin.com

I will report back.
0
 
LVL 3

Author Comment

by:sypder
ID: 18877158
I updated the reverse DNS, so the word naughty does not appear anywhere, and still it is not delivered to Hotmail.
0
 
LVL 32

Expert Comment

by:r-k
ID: 18877698
"I updated the reverse DNS, so the word naughty does not appear anywhere, and still it is not delivered to Hotmail."

Remember it may take over 24 hours for changes in the DNS to propagate to hotmail or other sites.

I assume you tried with Telnet and got the same transaction as before?
For comparison you may want to try the telnet test with other sites (yahoo, gmail e.g.) to see if that works any differently.
0
 
LVL 3

Author Comment

by:sypder
ID: 18877714
Yeah, I gave it more than 48 hours.

So, I sent the indentical email, in every way, except from a different IP, and it went through without problems.

So I guess my IP is on a blacklist (which is weird given that I haven't sent any emails from it in about 3 months) Maybe the person before me did bad things, or maybe Hotmail blacklist is just messed up.

I will figure out how to divide points shortly. Thanks for all the help, I learned a lot.
0
 
LVL 32

Accepted Solution

by:
r-k earned 300 total points
ID: 18877771
"So I guess my IP is on a blacklist .."

That's what it does seem like. I would contact hotmail support and try to get them to remove you. They doubtless maintain their own blacklists.

Many of these big ISP's will automatically remove you from the blacklist after a few months, but you can never be sure how long that time is.

Good luck.
0

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