Alas, I dont think that there is much you can do to prevent the confirmation dialogs with Outlook's MAPI dll. MS added them in a service pack as an anti-virus measure, so no work-around. Not all clients show these anoying dialogs though. Thunderbird definately doesn't.There is actually a workaround. You're using Simple MAPI which has a nice easy interface. The confirmation dialogs are only for Simple MAPI. Using Extended MAPI can work around the problem but its a lot more tricky.
See the initial discussion here: http://aspn.activestate.com/ASPN/Mail/Message/Python-win32/2160646
This code has now been included in pywin32 somehow but I can't remember where and its late. Should also be a cookbook entry. Maybe Google can help :-)
Cool. I'll take a look an' see if I can get it to work. MAPI has turned out to be a major PITA. Especially when trying to learn it and Python at the same time. :)
Chris -- http://mail.python.org/mailman/listinfo/python-list