Apple has just released a new version of their ITunes software (7.6) that includes a new version of their calendar synch add-in. The new version seems to fix all the previous problems with Outlook crashing or hanging after synching calendars, causing problems for other add-ins, and in crashing Outlook when connected or disconnected using the COM Add-Ins dialog.
If you sync your Outlook calendar with iTunes, you should install this update.
An Outlook Add-in Bug
Published January 17, 2008. Last updated on June 7, 2021.