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 as “I’ L” and beep, not allowing me to enter any new characters until I delete the old and I have to type “I am” or “I will”. “I’ve” is also a problem. It’s seems as if the auto spell checker is just choking on any contraction beginning with “I”?
This issue is now resolved in Mavericks.
Users running older versions of OS X, can use this work around:
Turn off the “Capitalize first letter of sentences” autocorrect setting.
Select the menu Outlook, Preferences, Autocorrect and uncheck “Capitalize first letter of sentences”.
[Added Dec 16, 2013] User, syncline posted this solution on Ars Technica Forum. View forum post]
I’ll add my confirmation on this! Here’s what I’ve been able to figure out so far.
1) New emails (originating with me) with HTML formatting do not have the issue.
2) New emails (originating with me) NOT in HTML format show the above behavior
3) Responding to non HTML emails in the same format (i.e. responding back without HTML enabled) show the above behavior.
4) Responding to non HTML emails in HTML format do not have the issue.
The issue appears to be entirely with non HTML formatted emails.
Solution – Go to Outlook Preferences and select ‘Composing’
At the bottom of the window pane under Format and Account turn on ‘Compose messages in HTML by default’
Turn OFF ‘When replying or forwarding, use the format of the original message’