Cannot send mail to a group if hiding addresses

I can't send mail to a group unless I show all member addresses. If I uncheck this preference I recieve the following error dialogue:
This message could not be delivered and will remain in your Outbox until it can be delivered.
Sending the message content to the server failed.
Very frustrating and infuriating for my reciepients. Any ideas?
MacBook Pro   Mac OS X (10.4.9)   2.16 GHz Intel Core Duo - 1GB 667 MHz RAM - 100GB

Thank you Klaus,
In mail help, Bcc is indicated as an alternative to unchecking the box saying show names in group when sending. Any ideas as to why the preference doesn't work?
MacBook Pro   Mac OS X (10.4.9)   2.16 GHz Intel Core Duo - 1GB 667 MHz RAM - 100GB

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