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Exchange 2003, Some Mail is Not Getting Through

We have Exchange 2003 on a SBS 2003. We have had this for many years with no problems. About 3-4 weeks ago, we stopped receiving any e-mail. At that time we were using Trend's Hosted E-mail and all of our mail was sitting there. NDRs for the mail would indicate, "timed out while sending end of data." We had an "expert" come in to look at the problem and he took Trend HES out of the picture. After that, most, but not all, of our mail started coming in. He said there was no reason he could find that our mail was not coming to us. He suggested we have our mail go to an outside server and then that server could forward it to us, that way bypassing whatever is wrong with our Exchange system. The other option was to purchase a whole new server, etc. (That is not an option.)

We have NAT enabled on our router, but no firewall. We disabled the Trend HES, but there is still an anti-spam option on Trend that runs "in-house." I can see what mail that rejects, though, so that isn't causing this. Also, I did stop that to see if it would change and it didn't. Port 25 is open.

I have researched this and possible answers. I have:
1. Run the SBS best practises tool - nothing out of the ordinary.
2. I can telnet with no problem.
3. DNS Report results don't show any problems.
4. I did netdiag with nothing out of the ordinary.
5. I tested at MX Toolbox and those tests said everything was fine.
6. I have searched Experts Exchange and tried everything I could that was suggested here.

Of note:  in the smtp virtual server, current sessions, there are quite a few items that just sit there. A lot of those look like legit email that we never get. I have attached one of our email logs. It looks like a lot of those same e-mails are marked "timed out." Why would they do that and where do they go?

Any help would be so appreciated.
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Simon Butler (Sembee)

8/22/2022 - Mon
Simon Butler (Sembee)

Primary reason for email delivery failures on this version of Exchange is outside of Exchange.
AV/Antispam on the server itself. If you have file level AV for example then it should have exclusions for the Exchange directories in it, so it isn't scanning anything.

Does the router do any SMTP scanning? This is a feature of some products and can get in the way.

Timeout is usually interference from something, and you have to step through the path to find the source of the interference. Usually local though, unlikely to be the ISP.


Thank you so much for your response, Simon. The AV is Trend. It does have antispam, but this happened even when I disabled that. I have no problem trying that again, though. As far as anti-virus, it does exclude Exchange directories.

The router does no scanning.

How do I step through the path?

I think I should say that we still have some windows 2000 computers on our system. This has stopped me from upgrading the Trend software (since it doesn't support that). Trend just recently updated the product (Worry Free), but I can't do the update because clients have to be, I believe, xp or higher. I believe the update for Trend came out just after I started having this problem.

One other thing I did find on Experts Exchange that I didn't do (a little afraid) was to update the drivers on the NICs. We have two. I do believe that both have updates but I'm afraid if I do that I'm going to make things so much worse. The person who came in to look at this didn't seem to think that was necessary. But if this is caused by interference, the NIC could be the culprit, right?
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Simon Butler (Sembee)

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