Some recipients receive multiple copies when >3MB attachments

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Tim - 06 Feb 2008 14:01 GMT

Help!

I'm not sure if this is an Exchange or Outlook issue. When sending emails
with large attahcments to internet addresses on a large distribution list,
some of the recipients get the email 20 or 30 times. Here's what I know:

Exchange 2003 Enterprise SP2 Version 6.5 build 7638.2 SP2 running on WIndows
2003 Enterprise edition SP2

Symantec Information Foundation Mail Secruity for MS Exchange v 6.0.3.201
running with the Premium Antispam addition.

Symantec Antivirus v10.0.6.6000 running on the server.

Senders are using Outlook 2003 that is fully patched. There are three users
that are having this issue.
They are sending to many different internet email addresses. Only a few
recipients are receiving it multiple times. There does not seem to be a
pattern based on email domain.
I don't know the mail server/client of the recipients.
Outbound mail is not using a smarthost
Outbound mail is not being scanned by AV at the client or server as far I as
can tell.
This does not happen if sending to a single email address. Only when there
are multiple recipients.
I did ask the senders to change the server timeout from the default of 30
seconds but they have not had to do any more bulk emails with large
attachments.

The customers are getting very annoyed that their mailboxes are filling up
and then rejecting mail.

Thanks,
Tim Lange

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F.H. Muffman - 07 Feb 2008 05:57 GMT

> I'm not sure if this is an Exchange or Outlook issue. When sending
> emails with large attahcments to internet addresses on a large
[quoted text clipped - 25 lines]
> The customers are getting very annoyed that their mailboxes are
> filling up and then rejecting mail.

Well, I'm going to make 2 assumptions.

1) That the mail messages are being sent via Exchange and not via an SMTP
server (ie, there is no pop/imap/web mail set up in the profile in Outlook)
2) That you have admin access to Exchange.

Check the logs on the Exchange server. Are multiple messages being sent
out of the server? Are multiple messages being submitted by the client if
you look at Message Tracking?

Signature

-f.h

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Tim - 07 Feb 2008 13:02 GMT

Your assumptions are correct. Messages are sent via Exchange and I have
admin access. Message tracking was not turned on, but it is now. So far,
no more bulk emails have been sent out, so there's nothing to check in
message tracking. I'm not on site for this customer to check the logs.
We're waiting for the next go-round and then we'll check to see if Exchange
is sending multiple messages. According to the admin there, the messages are
not stuck in the user's Outbox so they appear that they've been successfully
sent to the Exchange server.

Tim

> > I'm not sure if this is an Exchange or Outlook issue. When sending
> > emails with large attahcments to internet addresses on a large
[quoted text clipped - 35 lines]
> out of the server? Are multiple messages being submitted by the client if
> you look at Message Tracking?

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michaelscholtz@gmail.com - 13 Mar 2008 09:40 GMT

I have the same issue.
Am on my way there now to look what they are using for AV protection
as this is now my primary suspect.
My initial thoughts where that is could have been caused by over size
mails but it seems to be happening with small messages too ( 36K )

Any resolution on this from your side ?

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Chuck - 11 Jun 2008 18:15 GMT

This could be caused by using 'RULES' on the recipients Outlook. I had a similar problem with text messages being sent to my email acct from a cell phone. Sometimes the RULE process gets stuck in a loop when it can’t see the ‘end of file’ tag on an email (corrupt from sender, or in my case text messages don’t always come through with it) and when I process it through a rule it just keeps processing and spitting out duplicates to that folder.

Here is how I resolved.

In OUTLOOK:

1. Go to the Tools Menu
2. Select Rules and Alerts
3. Double click your rule in the Rules and Alerts Window
4. After the rule is open, select next to go to the Select Action(s) window.
5. Select Stop Processing More Rules
6. Click Finish
7. If you have multiple rules, you may need to repeat this cycle for each rule that you have active.

Obviously if the email is not affected by a rule that is in place (such as move large files to this folder, etc) you will have to further investigate. Hope this helps someone.

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