@Jeff - See my article on obviating the restart prompt in Outlook to understand the behavior - http://blogs.technet.com/b/exchange/archive/2011/01/24/obviating-outlook-client-restarts-after-mailbox-moves.aspx.
@Prescott - The issue is due to the behavior of Outlook not applying updated Autodiscover settings when it has an existing connection. That's why prior to SP2 RU3, clients would not update in a cross-site db *over event. What we did in SP2 RU3 essentially is to force the RPC Client Access service to reject the connection, which kicks Outlook into do a profile discovery (in case of OL2007 and later via Autodiscover) and to apply all the settings to try and get a connection re-established. And due to the way Outlook caches information about the mailbox session (see the article I pointed Jeff to) there is no way to not have the restart prompt.
Ross