E-mail attachments not sending thru exchange 2003

Hi all.
I have installed a new SBS 2003 sever (exchange 2003).
The server are sending E-mail thru the ISP SMTP relay server.

We have run into a strange problem. Only some of the .PDF attached files are not delivered to the intended location, others are. The mail does reach the recipient without the attachment.

It is very unlikely that it is blocked by a spam filter on the recipients side as it is doing the same on different domains even if the PDF is zipped.

If anyone have any ideas on what to try.
please let me know.
Who is Participating?
Tomas ValentaIT ManagerCommented:
in Default SMTP Virtual server properties enable logging, in properties/advanced check all options, then send e-mail with attach. to wrong domain and look in  C:\WINDOWS\system32\LogFiles\SMTPSVC1\......latest log file for communication with remote host. Here you can see if transaction is succesfull, if the attach. was send,...
If the e-mail goes OK, then you must ask provider of your SMTP relay server.
Other question - do you use firewall between your e-mail server and SMTP Relay server ?
If yes, what type ?
Shabarinath RamadasanInfrastructure ArchitectCommented:
Check which spam filter is doing this filter. Speak with their admin to white-list your domain.

In the mean time, try with removing the extension of zip file to txt and send it.

Good luck
Tomas ValentaIT ManagerCommented:
If you turn on detailed logging in SMTP service you can find here more info from log.
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Have you got Exchange Intelligent Message Filter (IMF) turned on?

Michael WorshamInfrastructure / Solutions ArchitectCommented:
How large are the PDFs you are trying to send?

Setting Size Limits for Messages

Also remember that if the site you are sending to does not allow for large files attachments, then the receiver's domain mail server will also need to be tuned for allowing larger file transfer/attachments.
technolutionsAuthor Commented:
thanks for all the help guys,
IMF is on but I changed it to one. will keep an eye not it and see how it goes.
No errors in event log for SMTP.
I have changed the default attachment size with no luck. The size are not that big, average around 2-4Mb.
have you checked message tracking to see if the emails actually left your server ? or is it getting blocked somewhere along the line ?
technolutionsAuthor Commented:
The message itself gets delivered fine, only it gets striped of the attachment with some E-mails (not all)
Turn of IMF and send the email to test it that is the only way it will b e stripped unless you have a 3rd party anti-virus/anti-spam program on the server or client.
Michael WorshamInfrastructure / Solutions ArchitectCommented:
If the messages are getting delivered but attachments are getting stripped, most likely either your SMTP relay is doing it or the receiver has something that is preventing the files from incoming (i.e. front-end server checking for attachments or an anti-virus on the inbound server is removing the files).
technolutionsAuthor Commented:
My thoughts exactly Mw.
I enabled logging for the SMTP Virtual server and the messages with attachments are sending out "ok".
I have now changed the SMTP relay to use a different  server.
2 of the 3 account that had the problem are now sending attachments fine. Just waiting for confirmation from the 3rd account.
Looks like changing the SMTP relay server worked.
Thanks for the help.
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