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In ADUC, enable advanced features, then double-click the DL. Go to Exchange Advanced and ensure that the list is not hidden from the GAL. I doubt that this is the answer, but worth checking. There are no stupid questions, just stupid people - Mr. Garrison

I've had this happen on my Exchange server also. When I try to access the account in OWA, I get page cannot be displayed. To fix it, I wiped the account and recreated it, usually in a different information store or storage group. There are no stupid questions, just stupid people - Mr. Garrison

I've run into this so many times and the reason has always been that the recipient cannot accept the Email because their account is too small or too full. Have you tested the scenario with one of your own personal accounts? There are no stupid questions, just stupid people - Mr. Garrison

Check out this article: http://support.microsoft.com/default.aspx?scid=kb;en-us;843105 You may want to enable BCC Journaling like I did on my Exchange 2k server but editing the registry. You can see the BCC field in full-version Outlook. There are no stupid questions, just stupid people -...

support.microsoft.com/default.aspx?scid=kb;en-us;192185 Link didn't post right...try this one. There are no stupid questions, just stupid people - Mr. Garrison

Check out this link for database defragmentation/compaction instructions. I just ran this on my Exchange 2000 server and it reduced the sizes of my stores by at least 25%. I recommend that you do this once every 3 months. MAKE SURE that you use the backup option offered by the eseutil...

Try creating a contact in Active Directory for your Yahoo account. Enable advanced features in the Active Directory window, and then double-click on the new contact. Go to Exchange Advanced and hide the address from the Global List (so your other users don't see it). Then, double-click on...

You should add some more info to your post. You should have gotten a bounce-back Email from System Administrator with an error description at the bottom of the Email. Some possibilities are that the recipient cannot accept a 4MB attachment, or that their account is close enough to its limit...