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Probably the first kind of automatic alteration or correction of characters entered by the user by means of a keyboard, were “smart quotes”, i.e. the replacement of ' and " by proper typographic, localized apostrophe and quotation marks. The only candidate I can imagine coming earlier, is capitalization of the first letter in certain cases (still notoriously failing after abbreviation dots).

Soft keyboards today, especially on mobile devices with touch screens, do a lot more of that (and I do not mean Asian IDEs). For English and related languages, they may insert an apostrophe into a contraction entered without one (which is convenient, because that key is on a different shift level), e.g. isnt to “isn’t”, but at least iOS chooses “isn't” instead. They also don’t seem to do much “curlysation” elsewhere. The standard iOS keyboard at least gives access to the proper marks, Android does not.

So what could be a justified design rationale to make it harder for users to use more pleasing characters?

It is certainly not encoding or font issues. I know some users claim to prefer straight variants in some (sans-serif) typefaces, but I am looking for reasons other than typeface preferences.

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The most obvious explanation is that most people don’t care about correct punctuation marks in this respect—but people do care about having spelling corrected. People often have strong feelings about spelling autocorrect, but we don’t often see them complaining about "..." versus “...”.

Moreover, such issues are mostly relevant in documents to be distributed and possibly printed, rather than casual messages like e-mail and Facebook updates. When people write documents, they typically use—or at least have the option of using—a word processor, where they can have autocorrection of apostrophes and quotation marks. (This often results in wrong results, like “English” quotation marks used in texts in languages that have other conventions, just because the document language is by default English and the user does not care to change it.)

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    Good UX would require to make it possible for those who do care, though. It’s also not really the single author, but the many readers who matter. There must be a lot more people who are annoyed by ' rather than by . (And of course it’s bad UX to have word processors create documents in a manufacturer-set default language.) – Crissov Dec 9 '14 at 12:51
  • @Crissov, my parenthetic remark was mainly meant to point out that even people who write texts for a living quite often don’t care about quotation marks—even when they see, or should notice, all wrong quotes in their own text to be printed. Surely this is bad, but the question was about explaining the causes. – Jukka K. Korpela Dec 9 '14 at 13:12
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Search engines is a reason not to use smart anything.

Granted your app may never care about using a search engine but you asked a general question.

If someone enters can't as a search term on the keyboard and it does not find can’t they don't understand.

So you make the search engine to search multiple ways. It takes longer. What if I searched on can't, won't, and don't. That is now 8 searches.

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    Search engines and search functions have to deal with much more complicated things nowadays, e.g. Unicode normalization, so that really cannot be it. – Crissov Dec 9 '14 at 12:40
  • If this refers to web search engines like Google and Yahoo, they hardly pay any attention to punctuation. They generally skip non-alphabetic garbage when harvesting for their food: words! – Jukka K. Korpela Dec 9 '14 at 13:10
  • You asked for reason and that is A reason. – paparazzo Dec 9 '14 at 22:53

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