This baffles Matthew Carter, a type designer whose work spans everything from metal type’s last stand to digital’s first, and whose dozens of typefaces, like Verdana and Georgia, are viewed daily by a billion-odd people. “I have no idea why people don’t use proper quotes. They are always [included] in the font,” Carter says.

This lack of quote sophistication is odd, because the web’s design origins owe a lot to choices Steve Jobs made at Apple and later at his second computer firm, Next. Jobs’s attachment to type famously stems from a calligraphy class taken at Reed College, and he ensured that the first Mac had a mix of bespoke and classic typefaces that included curly quotes and all the other punctuation a designer could want. At Next, he went further, and the web’s father, Tim Berners-Lee, built the first browser and server on a Next.

But in the early days of the web, different computing platforms—Unix, Mac, and Windows, primarily—didn’t always agree with how text was encoded, leading to garbled cross-platform exchanges. The only viable lingua franca was 7-bit ASCII, which included fewer than 100 characters, and omitted letters from alphabets outside English and curly quotes.

Marcin Wichary, the current design lead at Medium responsible for pushing forward on typographic niceties, grew up in Poland, and says in his youth, most computers simply omitted his language’s ę, ł, and other diacriticals. He says he felt privately glad that his first and last names lacked a missing Polish letter. It took years before one of his middle names was easy to type.

But ASCII and a few similar small character sets acted as a limitation only early on. With the right effort, even by the late 1990s, a browser could properly show the right curly quotes. But effort is the right word: While browsers could show typographers’ quotes, it was hard for users to type them.

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Straight quotes appear as an abomination in a typeface, because their designers rarely love them; they’re included by necessity and often lack cohesion with other characters. The non-curly quote comes from the typewriting tradition, and arose from cost. As U. Sherman MacCormack wrote in The Stenographer in 1893: “For some time past the manufacturers of typewriters have adopted straight quotation marks, for the reason that the same character can be used at the beginning and end of the sentence, thus saving one key.”

At the time of the single quote’s popularization in the 1870s, the use of paired quotation marks was just over a hundred years old. Keith Houston, the author of The Book, has traced the history of many punctuation marks back hundreds and thousands of years on his blog Shady Characters, and in a book of the same name. “There was no quotation mark for a very long time,” he says. One first appeared in the third century BCE alongside the invention of basic punctuation. It resembled a right angle bracket, >, which was resurrected in the 1970s for quoting email without any apparent connection. (The history of that newer use of > remains undocumented.)