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Ok, so being a (La)TeX fan (most days) I'm also kind of a typography freak and I feel dirty when answering questions and typing boring "quotes" instead of the “educated” ones.

There is software that could automatically do this in the text, for example SmartyPants from the very same guy who created MarkDown, without messing with the code entered in questions/answers. I've also recently stumbled with BetterType which also sounds like a reasonable alternative. Either of these do not only do quotes but also dashes and ellipsis.

(As a side note, being on a Mac, I've just discovered that it's possible to type key combinations of Option [+ Shift] and [ or ] to get all kinds of quotes. But still it would be nice to have this consistently applied over all answers and questions on the site.)

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    I wouldn't like any such automatic conversion without the user having asked for them; it could mess with answers that (e.g.) talk about the quotation characters! As you observed yourself, it's quite easy (at least on Mac OS X) to type “quotes”—and dashes—when you want them; I use them several times a day. Surely if you care about using these characters, it's more worthwhile for you to learn how to type them on your system, so that they will work (almost) everywhere, rather than asking each website to implement automatic conversion features. Commented Aug 10, 2010 at 16:41
  • @ShreevatsaR: I agree in general but not in particular. Markdown can (and does, on SO) already mess up your posting when you don’t escape certain signs, e.g. when trying to show HTML code without marking it as code. The same applies here, in less severe. Commented Aug 10, 2010 at 19:42
  • @ShreevatsaR: But it's not just about me using the “smarty” quotes, it's about having them consistently used in the site. (Is that maybe too much to ask?) Commented Aug 10, 2010 at 21:41
  • @Juan: Yes, some people (see Andrew's answer below) don't want these quotes to appear in their answers, and they should be free not to use them if they choose. Given all the ways in which things can go wrong (it may turn out to be a nightmare getting the right "plain" character to appear), I think it would be more trouble than gain. Also, converting apostrophes interferes with text search in browsers: this is why Wikipedia doesn't use these characters, for instance. Commented Aug 10, 2010 at 22:14
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    Sorry but I don't buy any of these arguments. Andrew gave the reasons why he doesn't like them, and we have pointed out that these reasons are of little or no concern. If for some (extraordinary) reason one really needs to type a regular quote in the text (as opposed to code) there is absolutely no nightmare in typing \". And I think you give very little credit to engineers at Google; since long ago they properly deal with the whole set of unicode characters (Come on, they even index languages like farsi! And I know, Google is not the only search engine, but you see my point). Commented Aug 11, 2010 at 9:38
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    I said nothing about Google or search engines! I said text search in browsers: what happens when you hit Ctrl-f to find a word with an apostrophe. (BTW Chrome handles this “intelligently”; Firefox searches for what you typed.) Anyway, as a general principle, I don't like the idea of messing with what others type any more than necessary (Markdown is already too much sometimes, but it's a near-ideal compromise); if you like to see smart quotes and ellipses everywhere, it's quite easy to use in your own browser a script which takes care of this, instead of making every website implement it. :-) Commented Aug 12, 2010 at 0:18
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    Sorry, my mistake. I misread your last point. In any case, how often do you actually search by punctuation rather than by words? I still don't see any strong argument against this feature. And I don't want or care about every website implementing it, what I would like is the Q&A site for (La)TeX experts to show a little care about typography. Commented Aug 12, 2010 at 7:35

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Just to voice another opinion, I’m for this. Just about every blog software has it, so why not a site about typesetting?

I’m already annoyed at the fact that negative votes on SE are displayed using a hyphen - instead of the correct character. It would be nice to provide a minimum of nice typesetting to the users.

Unlike feared by Andrew, this doesn’t pose any technical problems (neither with cut&paste nor any other feature of the site).

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Actually, I loathe this sort of thing! Whilst it may look pretty, it causes a great deal of pain when doing cut-and-paste. That's slightly mitigated by the fact that most cutting-and-pasting will be of code, but still often one wants to quote something from the question in an answer.

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    Copy/paste already breaks on a lot of things though (you lose all other kinds of formatting, like code, italic or bold). Anyway, why would "real" quotes not work correctly when copy/pasted? Commented Aug 10, 2010 at 12:45
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    @jaif: formatting is one thing, characters are another. Special characters can get mangled in changes in character encoding. Commented Aug 10, 2010 at 14:01
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    +1 - I do a fair bit of cutting and pasting of Unix commands into SO, and a good thing about that is the possibility of the reader cut/pasting them. Commented Aug 10, 2010 at 15:13
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    @Charles: but you can do this. Commands should be marked as code anyway, so copy&paste will work just fine. In fact, the problem already exists when the user forgets to mark commands as code, as soon as they’re piping input from a file, and output into another. This: cat <foo>bar would be displayed wrong when posted in an answer without being marked as code. Commented Aug 10, 2010 at 19:45
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    I don't see the problem with copy&paste, if you copy the “funny” quotes from a question and paste them in an answer, they still work fine! Also there is no messing with encodings or anything, all pages produced by the site are UTF-8 encoded anyway! Commented Aug 10, 2010 at 21:44

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