When I am using automatic smart quotes, the Capitalize First Letter of Sentence feature doesn’t work properly if the first word of the sentence contains an apostrophe or a quotation mark. Furthermore, it won’t automatically capitalize the ‘I’ in words like “I’ll”, “I’m” and so on if I’m using curly quotes. The following example was typed without hitting the shift key once:
This’s how it looks when I am not using curly quotes. And now i’ve enabled curly ones. this’s how it looks now.