Problems when using contractions such as I'm, I'll, etc. Any help?

Rather than trash plist files, it's easier to check in a new User first with all new preferences to see if this fixes the problem.

Testing in a new User will quickly tell you if the problem is system wide or if it's your User's folder that contains the problem.

CREATE A NEW USER

Go to System Preferences --> Create a New User in Accounts. Switch to the New User by logging out/in or use Fast User Switching.

Open Office app for testing. It won’t be in the Dock in the new User. Go to Applications to open.

Do you still see the issue?

    If yes, then the problem is with your base files.

    If no, then the problem is in your User's folder.

As I wrote before, I found that there was a glitch hidden somewhere in the preferences (.plist) for Entourage that was causing the problem. All the solutions discussed before are work-arounds that help if you haven't managed to layer the problems too much with the electronic form of Band-Aid/sticky plaster in your attempts to solve the issue. Using autocorrect etc only works up to a point - you can sometimes end up with conflicts arising from too many auto-correcting corrections so to speak.

Best thing to try, worked for me 100%, and will refresh things anyway, is to throw away the preference files for Entourage, and maybe even Word and PowerPoint if things are really bad - then clean out your caches with something like Onyx. Throwing out preferences is a bit like starting your Office apps with a fresh slate. Doesn't damage anything, though it might be irritating if your frequently used corrections and set ups have to be installed again, but nothing as irritating as the problems everyone above has encountered.

So - my advice is to go user name/library/preferences….then scroll to the batch that starts with "com.microsoft…….." then throw out the Office Apps ones that end with " .plist " (this might look like gobbledegook, but if you navigate your way to the contents of the preferences folder, it'll all become clearer). If your problem is mild, you might solve it with just throwing out Entourage/Outlook or whichever app you are having problems with. The dramatic version of this is to take out anything that is a Microsoft programme .plist  (don't forget to store them in a folder, on your desktop rather in the trash so you can put everything back if it all goes pear-shaped). After removing the plists, restart the computer so that the new plists are built back, and you have a good chance of everything working properlyagain. I had persistent problems with "I'm" too and this managed to clear it.

Only Microsoft can give you a real solution. We are users just like you.

http://www.microsoft.com/mac/product-feedback

This is absolutely insane. Every time I attempt to type I'm it gets changed to I'M. Tried the solution in Autocorrect settings, but when I try to enter the apostrophe as an exception, it automatically adds a period to the end and doesn't work!!!!

You've got to be kidding me, right? A contraction as common as "I'm" is not recognized?!

Please give us a real solution, not a work around.

This is way too common and obvious to not have been addressed.