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A delegate sends an e-mail message on behalf of a manager in Microsoft Entourage 2004 for Mac or Microsoft Entourage 2008 for Mac. In this case, recipients who are listed on the blind carbon copy (Bcc) line do not receive the e-mail message.
Entourage uses the Send From command to specify that an e-mail message is sent by a delegate on behalf of the manager. However, the Send From command is an obsolete Simple Mail Transfer Protocol (SMTP) command. Therefore, Microsoft Exchange Server does not recognize it as a valid command. When Exchange Server receives the Send From command in e-mail headers, it cannot parse the command. This behavior causes Bcc recipients to be dropped when the e-mail message is delivered.
Microsoft has confirmed that this is a problem in the Microsoft products that are listed in the "Applies to" section.