At the Exchange Cabana
Toughest question so far:

How to restrict a specific group of users so that they can only e-mail certain people externally.

There doesn't seem to be an elegant solution for this currently. The 2 thoughts were:
1. Use an SMTP connector and implement restrictions on the connector. The problem is that SMTP connectors are not granular enough to apply to e-mail addresses - they only go to the SMTP domain level.
2. Create mailboxes for the external contacts/vendors and then set up an Outlook rule to automatically forward messages to the external e-mail address. The problem with this solution is twofold. First, it forces you to enable Automatic forwarding to the internet. Second, any replies to messages forwarded would go back to the mailbox, essentially forcing you to monitor that new mailbox.

It apppears the Exchange team will be taking this back to see if someting like this can be put into Exchange 12.
- posted by Ben Winzenz @ 8:54 AM