Straight quotes vs curly quotes: the fix for the most common typography tell

By Tracy Atkins, founder of BookDesigner.ai and BookDesignTemplates.com · 15+ years of print files, 70,000+ authors · Updated August 17, 2026

Why this small thing reads so loudly

Open almost any traditionally published novel and the quotation marks curve: opening marks curl one way, closing marks curl the other, and apostrophes lean right. That is the typographic convention readers have absorbed for decades without ever naming it. Straight quotes, the vertical marks you get from a typewriter or a plain-text file, sit at odds with that convention. Readers rarely articulate what is wrong, but a page full of straight quotes registers as unfinished, the same way a mismatched font or an odd margin does.

The frustrating part is that this is rarely a writing problem. It is almost always a paste problem.

Where straight quotes actually come from

Word's autocorrect, active by default, converts a straight quote into a curly one the moment you type it. So if the whole manuscript were typed fresh inside Word, you would likely never see a straight quote. The trouble starts when text arrives from somewhere else:

• Pasting from a plain-text editor or a code editor, which has no concept of smart quotes at all
• Pasting from some notes apps, which store text as plain text underneath a friendly interface
• Copying out of a PDF, where quotes often extract as straight marks regardless of how the PDF displays them
• Text that passed through an older document format or an export/import step that stripped formatting

Every one of those routes drops straight quotes into the document as literal characters, and Word's autocorrect has no reason to touch them, because as far as Word is concerned, that text was never typed.

Why autocorrect does not clean up what is already there

This is the detail that trips up most authors: autocorrect is a typing-time feature, not a document-wide cleanup tool. It watches your cursor and converts the character right as you press the key. Once a straight quote already exists in a paragraph, whether it was pasted in yesterday or three drafts ago, autocorrect has no ongoing reason to revisit it. You can retype a sentence next to it and get perfect curly quotes while the pasted line above stays straight forever, untouched, unless you do something about it.

This is also why straight quotes tend to cluster. They are not scattered evenly through a manuscript; they show up in blocks, usually wherever a chapter was drafted somewhere else and brought in, or wherever dialogue was quoted from an email, a text message screenshot transcribed by hand, or a source document.

The fix: find and replace, not manual hunting

Manually scanning for straight quotes in a full manuscript is slow and unreliable; your eye slides right past them after the first chapter. The practical fix is a find-and-replace pass:

1. Confirm Word's "Straight quotes with smart quotes" autocorrect option is turned on.
2. Open Find and Replace, search for a straight double quote, and replace it with the same straight double quote character.
3. Do the same for the straight single quote/apostrophe.

That sounds like it does nothing, since you are replacing a character with itself. What actually happens is that each replacement is treated as a fresh keystroke, so the same autocorrect rule that converts quotes as you type gets triggered on every existing instance across the whole document at once. It is a document-wide version of the same rule that already worked on your new typing, applied retroactively in one pass. Some book formatting tools bundle an equivalent pass into their import step automatically, which is worth checking for before you do it by hand.

The apostrophe direction gotcha

Even after a clean quote-fix pass, one category of error tends to survive: apostrophes that open a word rather than sit inside one. Consider:

• 'Twas a dark night
• The class of '90
• Rock 'n' roll
• She said, "I'll be there," droppin' the g on purpose

An apostrophe at the very start of a word looks, to any automated rule, identical to an opening single quotation mark. Both are the same character position: the start of a quoted or contracted span. So the automated logic that correctly curls a normal mid-word apostrophe to the right will often curl a leading apostrophe to the left instead, because it reads that position as the open side of a quote rather than an apostrophe standing in for missing letters.

There is no reliable global fix for this pattern. No find-and-replace rule can distinguish "the class of '90" from a genuine opening quote at a glance, because the character and its position are identical in both cases; only the meaning differs. This has to be caught by eye during proofing, one instance at a time, correcting the direction manually wherever a leading apostrophe curled the wrong way.

A short checklist before your file goes to print

Related: Formatting a book in Word · Choosing book fonts · Embedding fonts in your PDF