We help IT Professionals succeed at work.
Get Started

Unable to send email to random domains, craigslist.org, Timeout after DATA

1,009 Views
Last Modified: 2013-11-30
I am unable to send emails to certain domains. I have found very little after intense googling.

System:
MS SBS 2003
MS Exchange 2003
Symantec Firewall - SUSPECTED WEAK LINK (horrid firewall)

Emails to random domains will sit in the exchange message que until they timeout. The RCPT domain I have been researching the most has been craigslist.org. As you can see if you get a DNSREPORT they are setup fine with a PTR, correct MX, etc. I know its not because of a external or internal blacklist.

I contacted the IT department at Craigslist.org and they said:

"We're seeing a whole lot of 'timeout after DATA from exchange.MYDOMAIN.com [IP]' in our message logs.
If you google that, you'll see that its most likely a network tuning issues at your end or a broken pipeline implmentation."

I am seeing the following in my smtp logs:
66.150.243.1, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 300344, 0, 48, 0, 0, -, -, 421 mxi1s.craigslist.org Error: timeout exceeded,
66.150.243.2, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 125, 0, 38, 0, 0, -, -, 220 mxi1s.craigslist.org ESMTP Postfix,
66.150.243.2, OutboundConnectionCommand, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 125, 0, 4, 0, 0, EHLO, -, exchange.protingent.com,
66.150.243.2, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 156, 0, 24, 0, 0, -, -, 250-mxi1s.craigslist.org,
66.150.243.2, OutboundConnectionCommand, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 156, 0, 4, 0, 0, MAIL, -, FROM:<Administrator@protingent.com> SIZE=1176,
66.150.243.2, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 203, 0, 6, 0, 0, -, -, 250 Ok,
66.150.243.2, OutboundConnectionCommand, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 203, 0, 4, 0, 0, RCPT, -, TO:<res-273932860@craigslist.org>,
66.150.243.2, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 250, 0, 6, 0, 0, -, -, 250 Ok,
66.150.243.2, OutboundConnectionCommand, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 250, 0, 4, 0, 0, DATA, -, -,
66.150.243.2, OutboundConnectionResponse, 2/8/2007, 0:50:33, SMTPSVC1, EXCHANGE, -, 281, 0, 35, 0, 0, -, -, 354 End data with <CR><LF>.<CR><LF>,
Comment
Watch Question
Expert of the Year 2007
Expert of the Year 2006
Commented:
This problem has been solved!
Unlock 1 Answer and 2 Comments.
See Answer
Why Experts Exchange?

Experts Exchange always has the answer, or at the least points me in the correct direction! It is like having another employee that is extremely experienced.

Jim Murphy
Programmer at Smart IT Solutions

When asked, what has been your best career decision?

Deciding to stick with EE.

Mohamed Asif
Technical Department Head

Being involved with EE helped me to grow personally and professionally.

Carl Webster
CTP, Sr Infrastructure Consultant
Ask ANY Question

Connect with Certified Experts to gain insight and support on specific technology challenges including:

  • Troubleshooting
  • Research
  • Professional Opinions
Did You Know?

We've partnered with two important charities to provide clean water and computer science education to those who need it most. READ MORE