troubleshooting Question

Intermittent issues with SBS Exchange 2003 standard

Avatar of Matthew Cioffi
Matthew CioffiFlag for United States of America asked on
5 Comments1 Solution686 ViewsLast Modified:
I could use some help in resolving some issues that I'm having with SBS 2003 stabdard and exchange server.
Event Type:      Error
Event Source:      MSExchangeTransport
Event Category:      SMTP Protocol
Event ID:      7004
Date:            12/23/2009
Time:            11:59:46 AM
User:            N/A
Computer:      ASIDC01
This is an SMTP protocol error log for virtual server ID 1, connection #103. The remote host "66.96.130.XX", responded to the SMTP command "mail" with "550 bosauthsmtp09: Host 66.89.41.XX: No unauthenticated relaying permitted  ". The full command sent was "MAIL FROM:<> SIZE=2404  ".  This will probably cause the connection to fail.

For more information, click

End user is reporting this message:
our message did not reach some or all of the intended recipients.

      Subject:  RE: blackberry

      Sent:     12/23/2009 12:00 PM

The following recipient(s) cannot be reached:

      'Matt Cioffi' on 12/23/2009 12:00 PM

            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.

            < #5.5.0 smtp;550 bosauthsmtp09: Host 66.89.41.XX: No unauthenticated relaying permitted>

Event Type:      Error
Event Source:      MSExchangeTransport
Event Category:      NDR
Event ID:      3018
Date:            12/23/2009
Time:            11:50:23 AM
User:            N/A
Computer:      ASIDC01
A non-delivery report with a status code of 5.4.0 was generated for recipient rfc822; (Message-ID <63858742CE041B44B4CD01BB97E5D01A0135C604@asidc01.AutomationSolutionsInc.local>).  
Causes: This message indicates a DNS problem or an IP address configuration problem  
Solution: Check the DNS using nslookup or dnsq. Verify the IP address is in IPv4 literal format.
For more information, click

So here are some details that might help.

We upgraded the firewall and added a second internet connection from a different vendor.  I have configured a static route for all SMTP traffic to travel across only one ISP.  That ISP is the original provider.  We did recently have to switch to a new IP range, so our external ip is new.    We have a Barracuda anti-spam fire wall setup and email hits that first, using NAT in the firewall.  I have the mx record set to and I have a DNS record as well pointing to the peoper address, 66.89.41.XX.  I'm thinking that I must have soemthing in the exchange server misconfigured, or is it possible that when we switched to the new range soemthing had to changed on that ISP's side?  In the example of error 1 a second attempt to send worked fine.  Several users havehad this issue.    What should I be looking at to resolve this issue?  Is there something in the SMTP settings that I messed up, maybe DNS entries need to be updated?  MXTOOLBOX reports that reverse dns does not match.  I have been using zoneedit to manage the DNS and MX but it seems like the reverse lookup goes to which is of course wrong.  Does XO need to change that?

Thanks and let me know what else you might need to help me, I'm going a bit out of my mind with this.
Join our community to see this answer!
Unlock 1 Answer and 5 Comments.
Start Free Trial
Learn from the best

Network and collaborate with thousands of CTOs, CISOs, and IT Pros rooting for you and your success.

Andrew Hancock - VMware vExpert
See if this solution works for you by signing up for a 7 day free trial.
Unlock 1 Answer and 5 Comments.
Try for 7 days

”The time we save is the biggest benefit of E-E to our team. What could take multiple guys 2 hours or more each to find is accessed in around 15 minutes on Experts Exchange.

-Mike Kapnisakis, Warner Bros