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Old 04-12-2007, 09:50 PM   #1
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Registered: Apr 2007
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SendMail wont send anything to Hotmail or Yahoo Users.

I have sendmail version: 8.13.4
I have the only modification I can remember doing is:

I can send emails perfectly to gmail accounts. Here is a sucessfull output of an email send to gmail:

Received: by with SMTP id l11cs366927wac;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received: by with SMTP id d14mr1879830wxb.1175187909424;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Return-Path: <>
Received: from ( [])
by with ESMTP id h40si1247663wxd.2007.;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received-SPF: pass ( best guess record for domain of designates as permitted sender)
Received: from ( [])
by (8.13.4/8.13.4/Debian-3sarge3) with ESMTP id l2TH58SJ005383
for <>; Thu, 29 Mar 2007 13:05:08 -0400
Received: (from root@localhost)
by (8.13.4/8.13.4/Submit) id l2TH51kd005299
for; Thu, 29 Mar 2007 13:05:01 -0400
Date: Thu, 29 Mar 2007 13:05:01 -0400
From: root <>
Message-Id: <>
To: undisclosed-recipients:;

This is a test of the body.

I originally thought the reason hotmail or yahoo didn't receive my emails was because I had no reverse DNS for the IP I was sending the emails out with. Therefore I had my VPS provider create one for my IP. It now reflects with the IP I use to send out emails (

Even after the reverse DNS in place, hotmail nor yahoo could recieve my emails. I am now pretty much stump as to why. I have googled and scanned various other solutions and I havent found anything.

Here is a verbose output of using sendmail to an hotmail address of mine:
Quote: Connecting to [] port 587 via relay...
220 ESMTP Sendmail 8.13.4/8.13.4/Debian-3sarge3; Thu, 29 Mar 2007 1 3:07:17 -0400; (No UCE/UBE) logging access from: []
>>> EHLO Hello [], pleased to meet you
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<> SIZE=15
250 2.1.0 <>... Sender ok
>>> RCPT To:<>
>>> DATA
250 2.1.5 <>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <>... Connecting to via esmtp...
050 220 Sending unsolicited commercial or bulk e-ma il to Microsoft's computer network is prohibited. Other restrictions are found a t Violations will result in use of equipment located in California and other states. Thu, 29 Mar 2007 10:07:17 -0700
050 >>> EHLO
050 ( Hello []
050 250-SIZE 29696000
050 250-8bitmime
050 250-CHUNKING
050 250-AUTH LOGIN
050 250-AUTH=LOGIN
050 250 OK
050 >>> MAIL From:<> SIZE=320 AUTH=<>
050 250 OK
050 >>> RCPT To:<>
050 >>> DATA
050 250
050 354 Start mail input; end with <CRLF>.<CRLF>
050 >>> .
050 250 <> Queued mail for delivery
050 <>... Sent ( < > Queued mail for delivery)
250 2.0.0 l2TH7HeD007332 Message accepted for delivery Sent (l2TH7HeD007332 Message accepted for delivery)
Closing connection to []
>>> QUIT
221 2.0.0 closing connection
The main thing that strikes out to me is that hotmail says "Queued mail for delivery" whereas Gmail normally says "OKAY". It seems as hotmail gets the email, and then decides it's no good. I don't know if my IP is blacklisted or I have to change something in my configuration from to my IP, or what I have to do.
Our team has been researching this and some answers would be much appreciated. Thanks.
Old 04-13-2007, 12:59 AM   #2
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Registered: Jul 2004
Location: Los Angeles, CA
Distribution: Fedora Core
Posts: 23

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I believe that Hotmail and Yahoo now want you to have an SPF record in DNS before they'll take your mail.
Old 04-15-2007, 03:19 PM   #3
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Registered: Apr 2007
Posts: 10

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An update: Yahoo now works.
Hotmail does not.

I even followed the exact SPF records as MSN postmaster recommends.


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