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I have 2 users that occasionally receive emails with a pdf attachment that is not actually on the email. The paperclip will show in outlook but there is actually nothing attached. Accessing via owa shows an attachment but it appears corrupt.

I know the email is getting through our barracuda email filter because I can see it and download it from that dashboard with no problem.

Also, sending the exact email+attachment to a personal email address I have works fine. When I forward that email with the attachment to the users it also works fine.

Currently leaning towards it being an issue with outlook as opposed to exchange or barracuda spam filter but I could be wrong. A fair amount of google searching has turned up nothing, mainly issues with Outlook Express.

Also, corrupt attachments don't seem to be coming from any specific people, but when one won't come through resending doesn't resolve either.

If anyone has any ideas on this matter I would greatly appreciate it.

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3 Answers 3

up vote 1 down vote accepted

This was a well hidden KB article and I only found it on some old technet post.

Turns out it has to do with how some email clients form MIME-encoded messages that have inline attachments. Issue was resolved by running this command on Exchange Server 2007.

set-OrganizationConfig -ShowInlineAttachments:$true

However this is a little tricky as the reason that is off by default is because it does pose a minor security risk. I think at this point I'll leave it disabled and investigate on a case by case basis as it only happens on a very few select incoming emails. Wondering if anyone has any experience enabling this and if there is any arguments for or against it.

Links that support the resolution:

http://support.microsoft.com/kb/954684

http://social.technet.microsoft.com/Forums/en-US/exchangesvrclients/thread/478c326b-486b-461c-9141-dd544b245c75

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Nice catch Bolston32. –  KCotreau Jun 10 '11 at 23:10

It may be being blocked by attachment settings (it would be unusual for a pdf, but worth checking). You could try installing this add-on, Attachment Options for Outlook, and then adding the file type to the allowed attachments.

http://www.slovaktech.com/attachmentoptions.htm

If not, your corruption idea takes center stage.

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I doubt it's this, simply because 90% of PDFs comes through, but I'll go ahead and add pdf to the registry via the link support.microsoft.com/kb/938811 provided from your link. Thanks! –  Bolson32 Jun 7 '11 at 20:47

This may not be the issue in your case but many times users have asked why they see the paperclip when there is no attachment. It invariably turns out that the sender's signature includes an image, which Outlook sees as an attachment. If the PDF attachment is being stripped out for any reason, this may yet apply.

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It is definitely not a signature with an image, which is annoying btw, and I'm not sure if it is being stripped out. Currently entertaining the idea that it could be related to SEP, Honestly never thought about that but it's weird how things like virus protection slip your mind. Also seems to be localized to emails from less than 5 outside parties. –  Bolson32 Jun 7 '11 at 20:46
    
Wasn't the virus protection or outlook filtering the attachments. I still have no idea what it could be. –  Bolson32 Jun 8 '11 at 17:38

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