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Exchange 2003 repeatedly sending copy of mail

Posted on 2006-11-20
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Last Modified: 2008-03-18
Hi Everyone,

A mail with a large attachemnt was sent out on Friday from one of our sites. Since then, every 15 minuites the mail is being re-sent from the server. I've confirmed this by having a copy of the Header sent to me by the recipient.

I've checked the Message Tracking and there is nothing there, also the message only appears once in the sender's 'sent items'.

Can anyone please suggest where I could check next?

Thanks very much.
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Question by:Sunny-Brussels
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Expert Comment

by:Sembee
ID: 17979795
Inbound or outbound to your server? Is this an external message (ie coming over the internet by SMTP) or an internal message (Exchange to Exchange in the same org)?

If the message is very large then something could be rejecting it, but not rejecting it in the right way so that the message fails. It will probably be in queues somewhere, but as you haven't said what path the message is taking, further diagnosis isn't possible.

Simon.
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Expert Comment

by:Mark Galvin
ID: 17979818
Don't know if this is the answer you want / need but:
in ESM go to:
Admin Groups
First Admin Group
Servers
Expand your server
Expand Protocols
Expand SMTP
Right click on "Default SMTP Virtual Server
Under the Delivery tab it will tell you how many times it is going to try to deliever the message.

Is the message getting delievered each time it is sent?
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Author Comment

by:Sunny-Brussels
ID: 17979852
Thanks for your quick reply Simon. Here's some more info.

Message is outbound from my server, over the internet by SMTP to a customer's server.

The message is being accepted by the recipient's server and delivered to his inbox.

I'm looking at the queue and can see nothing 'stuck'.

Thanks very much,

Noel
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Author Comment

by:Sunny-Brussels
ID: 17979928
Pappaslim,

Thanks for your reply.

Yes, the mail is arriving in the recipients mailbox.

I checked the setting you mention above and indeed after the first and second try the server will subsequently try every 15 mins. The Expiration Timeout is set to 2 days, problem is that the message was sent on Friday so the 48 hour period is long over.
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Accepted Solution

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Sembee earned 500 total points
ID: 17980077
You need to see the message headers of the messages being received at the other end.
Specifically you need to know if they are identical.
If they are identical, same times on the server hops etc, then the repeat is taking place at the recipient's end.
If they are not identical, so each message is unique, then the problem is your server is resending the message.

That could be caused by something interfering with the message flow, particularly if it is a large message. Firewalls, anti spam and anti virus applications can cause this problem as they take so long to scan the message that it times out or the sending server thinks there is a problem and tries again.

Simon.
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Author Comment

by:Sunny-Brussels
ID: 17980719
Thanks Sembee,

I'd only looked at one header so I asked for several, and in fact the date and time that the mail was sent from my server remained the same on them all. The only correct time was between the recipients ISP and his own server.

I've sent the info to the recipient and told him to get hold of his ISP.

Thanks for all your help.




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