The trouble with being a former typesetter is that every day online is a new adventure in torture. Take the shape of quotation marks. These humble symbols are a dagger in my eye when a straight, or typewriter-style, pair appears in the midst of what is often otherwise typographic beauty. It’s a small, infuriating difference: “this” versus “this.”

Many aspects of website design have improved to the point that nuances and flourishes formerly reserved for the printed page are feasible and pleasing. But there’s a seemingly contrary motion afoot with quotation marks: At an increasing number of publications, they’ve been ironed straight. This may stem from a lack of awareness on the part of website designers or from the difficulty in a content-management system (CMS) getting the curl direction correct every time. It may also be that curly quotes’ time has come and gone.

Major periodicals have fallen prey, including those with a long and continuing print edition. Not long ago, Rolling Stone had straight quotes in its news-item previews, but educated them for features; the “smart” quotes later returned. Fast Company opts generally for all “dumb” quotes online, while the newborn digital publication The Outline recently mixed straight and typographic in the same line of text at its launch. Even the fine publication you’re currently reading has occasionally neglected to crook its pinky.

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.)

Scribes and printers chose different symbols and conventions, Houston says, until a regular comma and an inverted one—one rotated 180 degrees—used in the left and right margins came into vogue as “quotations marks” in 1525. “You’d see it on the outer margin or inner margin depending on who printed it,” sometimes pointing toward and sometimes away from the text.

But it took Samuel Richardson to make a consistently used paired set within the text. While he remains best known for his invention of the epistolary novel in English with Pamela in 1740, followed by other literary innovations, his trade as a printer long predated his novel writing. Until he came along, quotations remained marked in the margin for each line that contained any referenced text, not the starting and end point of the quote within the text itself. (It was also commonly used only for excerpts from other documents, not dialog.)

In the 1748 edition of Pamela, however, Richardson included not just these per-line commas, but also what we see as an opening quote and mirrored closing quote at the beginning and end of excerpts at the exact start and end in the run of text. The pairing and intraline practices quickly became standard, although it varied in style among countries. French writing instead features guillemets, « and », close relatives of the ancient > mark.

Typesetters likely first inverted commas until type foundries started casting proper quotes as separate pieces of type. When a “hot-metal” mechanized typesetter appeared in the late 1800s, it followed the tradition: The earliest Linotype keyboards had paired curly quotes and no straight ones. But practical typewriters, which began to appear around the same time as the Linotype, followed a different path. As a tool for note-takers like stenographers, telegraphers, and business secretaries, the typewriter had no need for the flourish of the curled quote—and it would have added cost, as MacCormack noted.

As metal typesetting equipment moved on an inexorable path towards extinction, typewriters begat teletypewriters, and those begat computer keyboards. Medium’s Wichary, at work on a book about keyboards, says he’s found just one computer keyboard that has curly quotes instead of straight: the Xerox Star 8010. Virtual keyboards have mostly followed the physical style.

Paul Ford, a writer and programmer known for his thoughts about how code affects culture, notes that even on a mobile device “the energy to type a curly quote feels prohibitive. You have to hold down the quote. The effort of typing one on a regular keyboard [also] can be prohibitive.” Some software automatically swaps in the “smart” quote, but doesn’t always get the right curl (decades should always be ’90s, but autoformat software often drops in ‘90s). For wonks, you can find cheatsheets for explicit shortcuts on desktop machines, like Shift-Option-] for a curly apostrophe on the Mac, but it requires additional effort and memorization.

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Even when a writer gets things right, the CMS remains a stumbling block. “Smart quotes are traditionally one of the things that get turned into weird garbage characters when the character encoding is set poorly,” Ford says.

The result of the variation in input from Word documents and other sources, explains Claudia Rojas, Fast Company’s website product manager, led that publication’s website (but not print publication) to standardize on straight quotes for consistency. Fast Company doesn’t seem alone, as any survey of sites quickly finds others that have made the same choice. As Greg Knauss, a humorist and programmer who has built CMSes, elaborates: “If you use [straight] ASCII quotes, you know that they’re going to survive the cut-and-paste transition that often happens with text, as well as old or broken email servers and other 7-bit indignities.”

Straight quotes are a way to play things safe, in other words—but they’re not the only solution. Wichary has taken the opposite tack at Medium, developing code to guess a user’s intent as they type and format quotes automatically. “We took it further than I originally thought was possible,” he says, and estimates the site covers about 95 percent of possible situations. “A fraction of people who type rock ’n’ roll ask, ‘Why do those point the same way?’”

Conceivably, if they wanted to, all CMS designers could employ algorithms to always make the curl happen. It’s ultimately a software choice when quotes either all get converted to typewriter versions or remain inconsistent in the final product. Because of this, there’s a temptation to read the push toward straight quotes as a principled, pragmatic stand against the needless embellishment of a curl. But Anil Dash, once the chief evangelist of Six Apart, makers of Movable Type, argues there’s a different underlying issue with the current generation of widely used CMS software. “Typography is the kind of refinement that happens at the end of a generation of CMS tech,” he says.

While it might seem that CMSes—like WordPress and others—are mature, Dash says periodicals’ systems are in the midst of continuous updates to deal with all the formats required by content partners: Facebook’s Instant Articles, Google’s support for Accelerated Mobile Pages (AMP), Apple’s News feed requirements, and others. “Once this stuff is nice and boring in a year or two, their developers will probably refocus on type and layout details,” Dash says.

So perhaps curled quotation marks will again have their day. Or, by then, it’s possible conventions will have changed enough that people cease to notice. Wichary says in Poland, the lack of Polish-style quotation marks („ and ”)  have led the current generation to use American-style quotes and think the native ones look wrong.

Maybe periodicals, which sometimes commission typefaces or pay to adapt existing ones, will demand type designers draw better-looking, harmonious straight quotes that don’t seem pulled from typewriter typebars. Paul Ford is just plain resigned: “They sure do look nicer to old people like you and me, but frankly do they actually add any magical semantic value to a given text? Not really.”