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

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>,
cchyperAsked:
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SembeeConnect With a Mentor Commented:
It looks like classic firewall interference. Check whether there is any SMTP scanning features built in and disable them.

Simon.
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bdeterdingCommented:
This is not overly helpful, but mostly just to chime in. Symantec FW does fall very short in many areas - that is why Symantec stopped selling it. I am reasonably confident it proxies email out - so the logs from the FW should be insightful.
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