I know Outlook ALWAYS behaves, but just in case you need a little help in troubleshooting, I almost always default to a command line. (I know it is the DOS or CPM in me coming out...) There are some nice ways to use a command line switch to make Outlook do some things that are IMHO harder to do from the UI... Enjoy!

http://support.microsoft.com/kb/296192/

http://www.outlook-tips.net/beginner/switches.htm