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Suppose there was a user of one of these sites whose handle was Won't. How would one form the possessive of this username to refer to that user's post?*

Won't's answer

Given that the 's possessive construction is apparently derived from a contraction, and the existence of a fair number of double contractions, I suspect this first one might be correct, but frankly, it looks weird to me.

Won'ts answer

One apostrophe in its usual place looks a little better to me, but it also looks like it might be a pluralization,** even though that doesn't make sense in context. This choice might read confusingly.

Wont's answer

This seems to be a non-starter, since it changes the name for the sake of forming the possessive.

Is the first one right, or is there a possibility I've missed?*


*Aside from using "the post by Won't" or similar rewriting.
**Especially given "Do's" and "don'ts" or "do's" and "don't's"?

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Your first formation (Won't's) is correct. It looks weird, perhaps, because it's an unusual situation, but there you have it. If somebody uses a contracted word as his/her username or handle, forming the possessive is going to look strange. Just gotta live with it!

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  • True, it's an edge situation. Any chance you have a reference source? "Always form the possessive with an apostrophe, no exceptions" -- Bloom Picayune Style Guide?
    – jscs
    Commented Nov 5, 2013 at 20:04

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