Question : Emails to msn and a few select domains fail due to time out

We moved physical locations and now have a new external IP address on an Exchange 2003 server (windows server 2003 standard)
Email addresses we previously sent to at Hotmail, MSN, Live are no longer making it through.
With more investigating, the first failed messages occurred two weeks before the more (when no changes had been made)

Many email conversations work perfectly.
In a three-way conversation between our domain, Gmail and Live.com
Gmail and Our domain receive all mail correctly.
msn does not receive mail from our domain but does see replies from gmail.

From our domain's exchange server.

Start > Run > CMD > telnet mx1.hotmail.com 25

220 bay0-mc5-f10.bay0.hotmail.com Sending unsolicited commercial or bulk e-mail
to Microsoft's computer network is prohibited. Other restrictions are found at h
ttp://privacy.msn.com/Anti-spam/. Violations will result in use of equipment loc
ated in California and other states. Tue, 17 Feb 2009 11:42:00 -0800
helo OURDOMAIN
250 bay0-mc5-f10.bay0.hotmail.com (3.8.0.31) Hello [OURIP]
mail from: kevin@OURDOMAIN
250 [email protected] OK
rcpt to: [email protected]
250 [email protected]
bdat 361 LAST
Date: Tue, 17 Feb 2009
To: [email protected]; [email protected]
From: kevin@OURDOMAIN
Subject: Testing Manual Telnet Email

Good Morning,

To correct an email delivery problem between us and your servers,
I am sending this email manually using a telnet session.

Please reply at your earliest convenience to help me troubleshoot this issue...
.......250 3d@bay0-mc5-f10.bay0.hotmail.com> Queued ma
il for delivery
quit
221 bay0-mc5-f10.bay0.hotmail.com Service closing transmission channel


Connection to host lost.

This Email is received from our exchange server by msn.  I can do the same to google.

Google and msn can reply and our domain email address receives both.

If I click reply-all from my domain outlook account,
The smtp log shows

65.55.37.120, OutboundConnectionResponse, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 16, 0, 309, 0, 0, -, -, 220 col0-mc4-f42.Col0.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 17 Feb 2009 11:55:23 -0800 ,
65.55.37.120, OutboundConnectionCommand, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 16, 0, 4, 0, 0, EHLO, -, OURDOMAIN,
65.55.37.120, OutboundConnectionResponse, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 31, 0, 66, 0, 0, -, -, 250-col0-mc4-f42.Col0.hotmail.com (3.8.0.31) Hello [OURIP],
65.55.37.120, OutboundConnectionCommand, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 31, 0, 4, 0, 0, MAIL, -, FROM: SIZE=6654,
65.55.37.120, OutboundConnectionResponse, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 47, 0, 35, 0, 0, -, -, 250 [email protected] OK,
65.55.37.120, OutboundConnectionCommand, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 47, 0, 4, 0, 0, RCPT, -, TO:,
65.55.37.120, OutboundConnectionResponse, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 78, 0, 24, 0, 0, -, -, 250 [email protected] ,
65.55.37.120, OutboundConnectionCommand, 2/17/2009, 11:49:28, SMTPSVC1, EXCHANGE, -, 78, 0, 4, 0, 0, BDAT, -, 6654 LAST,

But not no mail is received at Live.com address.

We can see the actual packets being sent out to the correct IP addresses from outside of the firewall.

Microsoft says

Hello Kevin,

 

My name is Brad; I work on the Windows Live Hotmail Domain Support Team, helping to support Hotmail's anti-spam efforts.  I understand you are currently experiencing mail deliverability issues sending to hotmail/msn. Our goal in Windows Live Mail is to make sure that every wanted message sent to Hotmail customers arrives in their inbox, and I know how frustrating it is when this doesn't happen.

I have investigated the IP DOMAINIP and found no issues with delivery to our servers.

Day
      

# Data
      

# Mails
      

# Inbox
      

# Deleted
      

# Junked
      

# RCPTs
      

RCPT Success %

02/16/2009
      

0
      

0
      

0
      

0
      

0
      

3,851
      

1.00

02/15/2009
      

0
      

0
      

0
      

0
      

0
      

3,245
      

1.00

02/14/2009
      

6
      

6
      

6
      

0
      

0
      

2,881
      

1.00

 

This is the only connections showing dating back to 02/05/2009.

If you have any further issues please feel free to contact us again.

 

Thank-you,

 

        Brad

Windows Live Hotmail Domain Support


So, I have no idea what to do.

Messages sit in our queue and retry until they time out on our server.

Answer : Emails to msn and a few select domains fail due to time out

GAH

As it turns out...
the internet email Auto-Protect function of
Symantec AntiVirus version 10.0.0.359
engine: 103.0.2.7
was selectively deleting data transmission packets to some domains (all mail to msn, hotmail, live, and some others)
and that service is not stopped then you disable the general auto protect.

After ENTIRELY disabling the anti virus software, the mail left the queue and was delivered successfully.