Sendmail Won't Send Mail To Hotmail Or Yahoo.

A better title might be "hotmail or yahoo won't accept the emails from sendmail."

I have sendmail version: 8.13.4

I have the only modification I can remember doing is:
MASQUERADE_AS(`ipalaces.org')dnl

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

Quote:

Delivered-To: paroxsitic@gmail.com
Received: by 10.114.113.11 with SMTP id l11cs366927wac;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received: by 10.70.80.14 with SMTP id d14mr1879830wxb.1175187909424;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Return-Path: <root@ipalaces.org>
Received: from ipalaces.org (ipalaces.org [64.74.153.24])
by mx.google.com with ESMTP id h40si1247663wxd.2007.03.29.10.05.09;
Thu, 29 Mar 2007 10:05:09 -0700 (PDT)
Received-SPF: pass (google.com: best guess record for domain of root@ipalaces.org designates 64.74.153.24 as permitted sender)
Received: from ipalaces.org (ipalaces.org [127.0.0.1])
by ipalaces.org (8.13.4/8.13.4/Debian-3sarge3) with ESMTP id l2TH58SJ005383
for <paroxsitic@gmail.com>; Thu, 29 Mar 2007 13:05:08 -0400
Received: (from root@localhost)
by ipalaces.org (8.13.4/8.13.4/Submit) id l2TH51kd005299
for paroxsitic@gmail.com; Thu, 29 Mar 2007 13:05:01 -0400
Date: Thu, 29 Mar 2007 13:05:01 -0400
From: root <root@ipalaces.org>
Message-Id: <200703291705.l2TH51kd005299@ipalaces.org>
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 ipalaces.org with the IP I use to send out emails (64.74.153.24)

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:

ek_opteron@hotmail.com... Connecting to [127.0.0.1] port 587 via relay...
220 ipalaces.org 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: ipalaces.org(OK)-ipalaces.org [ 127.0.0.1]
>>> EHLO ipalaces.org
250-ipalaces.org Hello ipalaces.org [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-EXPN
250-VERB
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5
250-DELIVERBY
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<root@ipalaces.org> SIZE=15 AUTH=root@ipalaces.org
250 2.1.0 <root@ipalaces.org>... Sender ok
>>> RCPT To:<ek_opteron@hotmail.com>
>>> DATA
250 2.1.5 <ek_opteron@hotmail.com>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <ek_opteron@hotmail.com>... Connecting to mx3.hotmail.com. via esmtp...
050 220 bay0-mc8-f1.bay0.hotmail.com Sending unsolicited commercial or bulk e-ma il to Microsoft's computer network is prohibited. Other restrictions are found a t http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Thu, 29 Mar 2007 10:07:17 -0700
050 >>> EHLO ipalaces.org
050 250-bay0-mc8-f1.bay0.hotmail.com (3.3.2.16) Hello [64.74.153.24]
050 250-SIZE 29696000
050 250-PIPELINING
050 250-8bitmime
050 250-BINARYMIME
050 250-CHUNKING
050 250-AUTH LOGIN
050 250-AUTH=LOGIN
050 250 OK
050 >>> MAIL From:<root@ipalaces.org> SIZE=320 AUTH=<>
050 250 root@ipalaces.org....Sender OK
050 >>> RCPT To:<ek_opteron@hotmail.com>
050 >>> DATA
050 250 ek_opteron@hotmail.com
050 354 Start mail input; end with <CRLF>.<CRLF>
050 >>> .
050 250 <200703291707.l2TH7DSt007328@ipalaces.org> Queued mail for delivery
050 <ek_opteron@hotmail.com>... Sent ( <200703291707.l2TH7DSt007328@ipalaces.org > Queued mail for delivery)
250 2.0.0 l2TH7HeD007332 Message accepted for delivery
ek_opteron@hotmail.com... Sent (l2TH7HeD007332 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 ipalaces.org 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 127.0.0.1 to my IP, or what I have to do.