Somehow, I managed to turn on the Smart (or "curly") Quote feature in Outlook today. Wasn't exactly sure how I did it, all I knew was I wanted it turned off. Outlook's help feature was useless and most of the results of my Google search said to use Plain Text instead of HTML formatted messages. The problem: I was already using Plain Text but still outputting Curly Quotes. Fortunately, deep down the search results page I found this message thread, which recommended the fix for dreaded curly quotes:\n\nCtrl+Shift+' (apostrophe) toggles them on or off. Mine are now set to OFF!