Most of the time Gmail lets me insert whatever characters I want into the subject or body of an email, but about a quarter of the time, it simply refuses to accept en or em dashes, and I have to revert to hyphens. It's so annoying, and it seems to do this at random.
This has been bugging me for ages, and I figured some other typophile here must have run into the same thing.
Other deets: It doesn't matter whether I'm in plain vs. rich text mode, or replying vs. composing anew. I don't know if it also would prevent me from inserting other nonstandard glyphs, but I'm guessing it would. (I tried to check just now, but it's not doing it right now.) I'm on a Mac, using Firefox. I tried finding an answer via google, but no luck.