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I have been tasked with programmatically creating a report and emailing it as an attachment every weekday. This was done fairly easily with a minor hiccup that has yet to be unravelled. The intended recipient, another company, is receiving the email but not the attachment. The attachment delivers fine internally. It delivers fine to third party email services such as Gmail and AOL mail (don't laugh). But, no matter what I try, it will not deliver to the intended recipient.
The automated script is written in Python 3.2 and uses our local Exchange 2007 server as an SMTP server. The message is being created with pythons "email" library and should conform to MIME standards (using MIME types in Python). The recipient has an Exchange 2003 server and both of us have Barracuda spam filters. The attachment does not seem to be being stripped from our spam filter, and the IT contact I have with the other company does not see it arrive at theirs. What could possibly be going on?

P.S. I have been unable to locate a duplicate problem through research, some similar but none quite the same.

yama arashi
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2 Answers2

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There are some incompatibilities between Exch2k3 and Exch2k7/10 with regard to the handling of MIME. I've seen this first hand from Exch2k3 -> Exch2k7, where the message arrives but Outlook cannot "see" the attachment. If you look at the message size as it hits the target gateway, the message would appear to include the attachment.

I haven't seen this from Exch2k7 -> Exch2k3. The issue only occurred when sending messages in RTF format (HTML and plain text were OK). I've just tried to locate an MS KB article, but only found Exch 5.5 hits. When looking in to this, the underlying problem was that the Exch2k7 handling of MIME was completely RFC compliant, suggesting that Exch2k3 had some slackness in its implementation. There was a work around for the Exch2k7 end, that is, to make it more slack, so to speak. However, I went down the "abolish RTF" route.

Can you confirm your message format?

Simon Catlin
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  • I edited the post to include how the message was being created, but it is a plain text message with a .txt file attachement. I am using Python's built in email module so it should be MIME compliant. – yama arashi Jul 15 '13 at 17:54
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The problem turned out to be some weird header issue with the email that was being sent. It is still confusing but following the guide from here I was able to get the email to go through to them. Prior to this change emails were showing up at third party email providers such as Gmail no problem just not to the company that needed them.

yama arashi
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