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When is the character limit on HN going to be increased so we can create longer subjects/headlines?

We're not going to do that, for a bunch of reasons. One is that it's a creative constraint which (after 15 years I think we can say) is always possible to work within.

Another is that if we made it longer, people would soon experience the new length as a constraint in its own right.

One trick is that HN also recommends we use the original headline from the piece posted. Whenever I have to edit it for length, I sometimes worry I'm going to be warned for editorializing a headline.

It's pretty obvious when someone has simply been editing to fit the length limit. That's legit.

Editorializing has to do with changing the meaning of a title—for example to put a spin or interpretation on it that the submitter wants to emphasize. On HN, submitters don't get to use the title field as a sort of mini comment box.

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