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PDF being received as winmail.dat

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I have Outlook 2010 using Exchange 2010. When I send an e-mail with pdf attachments to a recipient using Entourage on the Mac, this recipient receives the files as winmail.dat (in one container). I am sending this as HTML (not Rich Text). The domain of the recipient is a domain configured on the Exchange Server as an Internal Relay Domain, but this particular recipient has a mailbox on another server (not Exchange). This user has two domains on the remote server, and both are also configured as Internal Relay Domain on the Exchange server. When I send the e-mail to one domain, it gets the winmail.dat-treatment. When I send the same e-mail to the other domain (which actually arrives in the very same mailbox on the remote server), it does NOT get the winmail.dat-treatment. What can this be?

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