Send mail problem on exchange 2003

I tracked a mail which user reported recipient had not received. The mail had an attachment of 4 meg. The mail was in the users sent box. I used exchange message tracking and could see the log for the mail sent however when I clicked on the mail the logs were a little confusing, it looks like the mail is trying to send over and over
I get
smtp:started outbound transfer of message
message transferred to throughsmtp
smtp:started outbound transfer of message
message transferred to throughsmtp

and so on each moving to s different smart host at isp.

I have taken over this server and the previous person had trend micro suite installed.not sure if this has any affect.

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Sid_FAuthor Commented:
mail is no sending! : ) have since resolved this, was down to a malfunctioning firewall scan policy

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if it trend micro scans your outgoing mail then yes you should definetly check the configuration
are you sending via ISP smtp server?
if so, check with them if their server has mail size limitation.
Sid_FAuthor Commented:
Hi see above was down to scan policy on firewall
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