Our thoughts for our large organization: Skip the Exchange update tool; there's too many exceptions and it runs too slow (it would take us weeks to update all of our calendars, even with 6 simultaneous instances running.) Run the Outlook update tool via the logon script, inside of a VBS wrapper. First the VBS needs to make sure the OS patch is installed, then check to see if MAPI is set to prompt for profile upon starting Outlook (if that's turned on, silent mode isn't going to work.) If those tests pass, then run the Outlook tool in silent mode. Scrub the Event Log afterwards to see what appointments failed to be updated, then stick a pretty HTML email in the user's Inbox with a status report, and list which appointments they may need to touch manually (based on Event Log data.) If profile prompt is turned on, we launch the Outlook update tool in interactive mode -- we communicate ahead of time what to do when this happens. In either situation, we also log status for that particular user to a central location on the network, and that status is also checked the next time the user logs on to make sure it doesn't run twice. We'll use the central logs to also identify who hasn't logged on in a while, etc, and handle those on a case-by-case basis. We haven't been able to find any other way that works effectively in a large environment to get everyone updated quickly and accurately.