Strange Bouncebacks

Hi all.  I am trying to troubleshoot a strange issue with one of our client's Small Business Server - 2003 and 100% up-to-date with all SP's and updates.  Users keep getting strange bouncebacks and undeliverable mail lately such as:

ContactName on 24/01/2008 5:56 PM
There was a SMTP communication problem with the recipient's email server. Please contact your system administrator.
<mailgate.domain.com #5.5.0 smtp;501 <E>: sender address must contain a domain>

I work with alot of SBS 2003 sites but this is a new one on me!!  Any help greatly appreciated.

Cheers
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donmeadoAsked:
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donmeadoConnect With a Mentor Author Commented:
Hi all.  Apologies for the delay in reporting back.  We believe we have now found the cause - in mentioning the issue to Sophos, they admitted this as a known fault in one of their product builds of Puremessage (which this system runs).  After stopping Puremessage scanning outbound, this issue vanished.  I have now upgraded to the next Puremessage product build.  Thanks for all the suggestions.
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Michael WorshamInfrastructure / Solutions ArchitectCommented:
You might want to check to see if that SBS/Exchange server is setup as a relay server. I recommend testing that domain via www.dnsstuff.com and its DNS Report.
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donmeadoAuthor Commented:
Warn: Glue at parent nameservers.  WARNING. The parent servers (I checked with f.gtld-servers.net.) are not providing glue for all your nameservers. This means that they are supplying the NS records (host.example.com), but not supplying the A records (192.0.2.53), which can cause slightly slower connections, and may cause incompatibilities with some non-RFC-compliant programs. This is perfectly acceptable behavior per the RFCs. This will usually occur if your DNS servers are not in the same TLD as your domain (for example, a DNS server of "ns1.example.org" for the domain "example.com"). In this case, you can speed up the connections slightly by having NS records that are in the same TLD as your domain.

Fail: All nameservers respond.  ERROR: Some of your nameservers listed at the parent nameservers did not respond. The ones that did not respond are: 209.246.126.109  Note: If you are running a Watchguard Firebox with DNS Proxy enabled, there may be a bug causing port numbers get mixed up -- if this is the case, you can contact Watchguard to see if they have a fix.

Warn: Nameservers on seperate class C's.  WARNING: We cannot test to see if your nameservers are all on the same Class C (technically, /24) range, because the root servers are not sending glue. We plan to add such a test later, but today you will have to manually check to make sure that they are on separate Class C ranges. Your nameservers should be at geographically dispersed locations. You should not have all of your nameservers at the same location. RFC2182 3.1 goes into more detail about secondary nameserver location.

Warn:  TCP allowed.  WARNING: One or more of your DNS servers does not accept TCP connections. Although rarely used, TCP connections are occasionally used instead of UDP connections. When firewalls block the TCP DNS connections, it can cause hard-to-diagnose problems. The problem servers are: 209.246.126.109: Error [No response to TCP packets].

Warn: SPF record.  Your domain does not have an SPF record. This means that spammers can easily send out E-mail that looks like it came from your domain, which can make your domain look bad (if the recipient thinks you really sent it), and can cost you money (when people complain to you, rather than the spammer). You may want to add an SPF record ASAP, as 01 Oct 2004 was the target date for domains to have SPF records in place (Hotmail, for example, started checking SPF records on 01 Oct 2004).

Fail: Domain A lookup.  ERROR: I couldn't find any A records for antycip.net. But I did find a referral to www.antycip.net. (and maybe others). If you want a website at antycip.net (as well as www.antycip.net), you will need an A record for antycip.net. If you do not want a website at antycip.net, you can ignore this error.
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Michael WorshamInfrastructure / Solutions ArchitectCommented:
You also might want to check your external DNS setup is see if you have the correct A, CNAME and MX records as well.
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DrDave242Commented:
Never seen that one before, but the error in the bounceback message, "Sender address must contain a domain," makes it sound like your users' primary SMTP addresses aren't configured correctly.  Open the properties page of a user that's experiencing the problem, then select the E-mail Addresses tab.  Is the SMTP address in boldface in the correct "user@domain.com" format?
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donmeadoAuthor Commented:
Checked all - RDNS appears OK (several tools). A, CNAME and 3 MX records all appear OK. Checked in AD and primary addresses are all fine to - correct format.
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kieran_bCommented:
Your DNS and server itself seem fine...

Is this a problem with all senders?  All recipients?

If we can isolate it to a specific sender, sending to a specific domain, that would help.

Does the sender name contain a ' by any chance?
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DrDave242Commented:
You might want to turn on SMTP logging and send a few messages, then take a look at the log.  Here's an article that shows you exactly how to do it (and how to import the log into Excel so it's much easier to read):

http://www.msexchange.org/tutorials/Logging_the_SMTP_Service.html
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donmeadoAuthor Commented:
Seems to be both random senders and recipients.  I don't think the sender contains ' but I'll check this and try the logging and will report back...
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bundasCommented:
If it happenned to only certain clients (not all of the clients of the server), it might came from the account setting of the client program (Microsoft Outlook). Check if there is something wrong there. Might be a simple mistake.
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