Some users send .pdf attachments from a program called Fourth Shift. This has never been a problem in the past. The email shows up in the user's Sent Items in Exchange. Recently, some of these emails are being queued in our Barracuda Spam and Virus Firewall. The user gets no notification of this and the recipient never gets the message. We can not find any reason why some of these emails go through and others get queued. Sometimes we can resend a .pdf to the same email address and it goes through just fine.
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