Outlook for Mac 2011 has had issues with contractions since early November 2012 after Apple released v 6.0.2 Safari webkit update. The fix was released recently in the version of webkit included with Mavericks.
I’m having a problem whenever I try to use contractions that begin with “I” – such as I’m, I’ll, etc. When I type “I’m”, I get “I’ M” followed by a beep. Same thing with “I’ll” – Outlook will type it . . .
Continue Reading: Mavericks resolves issue with Outlook 2011 and contractions