I read this in Word by Word by Kory Stamper:

Teachers will write in and angrily ask how they can possibly teach their students proper grammar and punctuation if the dictionary can be bothered to use it? Even that is changing, however there is room online to put in both the subject and terminal punctuation, thereby (we hope) saving students of English from utter inevitable idiocy.

I want to ask why has the author written "and" in italics? Of course, there must be a subtle pun but I don't get what exactly it is.

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    The author used italics for emphasis. – Kreiri Sep 27 '19 at 11:54
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    @Kreiri Is right. In other words: there is no pun. – Dan Bron Sep 27 '19 at 13:27

It was already noticed that emphasis is the purpose, but the object of emphasis was forgotten in the explanations :)

The author wants to say this:

  • only one problem is already bad;
  • but two problems are a lot worse: "subject AND terminal punctuation".

In spoken language, we would pronounce "and" in a louder voice, just to underline that there is more than one problem.

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I mean I'm no expert, but it seems as though the "and" was italicized just to emphasize the annoyed tone of whoever is speaking. It doesn't necessarily have to be a pun. But, in case it is, I think what would help you is finding what "terminal punctuation" is. Maybe it's a technical term in English grammar or something.

If you doubt that it has been italicised to signify annoyance or an annoyed tone, I urge you to read a novel or browse through any comment section. This website I just found, for example, talks about it. I even remember seeing it in some news articles and some product reviews.

anyway, good luck.

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