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exchange 2003 delivery failures

i have a unique situation.  i have a user that is unable to send a particualr email with certain conditions.  the email is a small excel attachment.  that delivers interally perfectly fine, but fails externally.  actually it hangs in queue and eventually fails.

the user can email to individuals all day long but when you add mutiple people (3) to the recipient list with the attachment it never leaves the queue.

4.7.7 delay error connection dropped by host.

funny thing is that one of the domains this user sends to doesn't have any filtering enabled.  
it seems to be a failure on the sending server not the receiving server since it is for mutiple domains.

any help would be great.
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rather_b_fishin
Asked:
rather_b_fishin
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1 Solution
 
tolinromeCommented:
Are there details on the NDR? Have you checked the properties on the SMTP relay connector, any limits?
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Simon Butler (Sembee)ConsultantCommented:
Do you deliver email directly, or via a smart host?
What is between Exchange and the internet? A firewall? If so, what is it?

Simon.
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rather_b_fishinAuthor Commented:
directly.  nothing installed that is new.  same firewall as always no changes. (that i am aware of)  it is a cisco appliance.
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rather_b_fishinAuthor Commented:
4.7.7 delay.. then fails.
in the queue it specifies that the remote dropped the connection.
10 limits and no changes on the connector
the email in question is under 55k
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Simon Butler (Sembee)ConsultantCommented:
" it is a cisco appliance. "

I would point the finger at that.

Cisco devices have a feature called FIXUP SMTP or Mailguard, or something like that. Notorious for breaking email delivery. Can work for years and then start playing up with certain servers. Get the SMTP scanning functionality disabled.

Simon.
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rather_b_fishinAuthor Commented:
i read about that... is it per transmission? or based on address? or based on sender?
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Simon Butler (Sembee)ConsultantCommented:
No, it is a transport thing - it just gets in the way.
It is so notorious it even has an article on the MSKB: http://support.microsoft.com/kb/320027

Simon.
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rather_b_fishinAuthor Commented:
i have an email out to the datacenter we use that manages the firewall.  waiting on them to reply..

thanks
i will post the results.
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rather_b_fishinAuthor Commented:
sorry for the delay in rating
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