Typos can be embarrassing. They can also be costly. And not just for those individuals whose jobs depend on knowing the difference between “it’s” and “its” or where a comma is most appropriate. In 2013, bauble-loving Texans got the deal of a lifetime when a misprint in a Macy’s mailer advertised a $1500 necklace for just $47. (It should have read $497.) It didn’t take long for the entire inventory to be zapped, at a loss of $450 a pop to the retail giant. (Not to mention plenty of faces as red as the star in the company’s logo.)

Google, on the other hand, loves a good typing transposition: Harvard University researchers claim that the company earns about $497 million each year from people mistyping the names of popular websites and landing on “typosquatter” sites … which just happen to be littered with Google ads. (Ka-ching!)

Here are 10 other costly typos that give the phrase “economy of words” new meaning.

1. NASA’S MISSING HYPHEN

The damage: $80 million

Hyphens don’t usually score high on the list of most important punctuation. But a single dash led to absolute failure for NASA in 1962 in the case of Mariner 1, America’s first interplanetary probe. The mission was simple: get up close and personal with close neighbor Venus. But a single missing hyphen in the coding used to set trajectory and speed caused the craft to explode just minutes after takeoff. 2001: A Space Odyssey novelist Arthur C. Clarke called it “the most expensive hyphen in history.”

2. THE CASE OF THE ANTIQUE ALE

The damage: $502,996

A missing ‘P’ cost one sloppy (and we’d have to surmise ill-informed) eBay seller more than half-a-mill on the 150-year-old beer he was auctioning. Few collectors knew a bottle of Allsopp’s Arctic Ale was up for bid, because it was listed as a bottle of Allsop’s Arctic Ale. One eagle-eyed bidder hit a payday of Antiques Roadshow proportions when he came across the rare booze, purchased it for $304, then immediately re-sold it for $503,300.

3. THE BIBLE PROMOTES PROMISCUITY

The damage: $4590 (and eternal damnation)

Not even the heavenly father is immune to occasional inattention to detail. In 1631, London’s Baker Book House rewrote the 10 Commandments when a missing word in the seventh directive declared, “Thou shalt commit adultery.” Parliament was not singing hallelujah; they declared that all erroneous copies of the Good Book—which came to be known as “The Wicked Bible”—be destroyed and fined the London publisher 3000 pounds.

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4. PASTA GETS RACIST

The damage: $20,000

A plate of tagliatelle with sardines and prosciutto would typically only be offensive to a vegetarian’s senses. But an unfortunate blunder in The Pasta Bible, published by Penguin Australia in 2010, recommended seasoning the dish with “salt and freshly ground black people.” Though no recall was made of the books already in circulation, the printer quickly destroyed all 7000 remaining copies in its inventory.

5. JUAN PABLO DAVILA BUYS HIGH, SELLS LOW

The damage: $175 million

Online trading was still in its relative infancy in 1994, a fact Juan Pablo Davila will never forget. It all started when the former copper trader—who was employed by Chile’s government-owned company Codelco—mistakenly bought stock he was trying to sell. After realizing the error, he went on a bit of a trading rampage—buying and selling enough stock that, by day’s end, he had cost the company/country $175 million. Davila was, of course, fired. And Codelco ended up filing suit against Merrill Lynch, alleging that the brokerage allowed Davila to make unauthorized trades. Merrill coughed up $25 million to settle the dispute—but not before a new word entered the popular lexicon: davilar, a verb used to indicate a screw-up of epic magnitude.

See Also: 8 Psychological Tricks of Restaurant Menus

6. MIZUHO SECURITIES SELLS LOW—LIKE, REALLY LOW

The damage: $340 million

In December 2005, Japan’s Mizuho Securities introduced a new member to its portfolio of offerings, a recruitment company called J-Com Co., nicely priced at 610,000 yen per share. Less than a year later, one of the company’s traders made more than a simple boo-boo when he sold 610,000 shares at one yen apiece. No amount of pleading to the Tokyo Stock Exchange could reverse the error.

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7. CAR DEALERSHIP PULLS A MICHAEL SCOTT

The damage: $50 million (or $250,000 in Walmart dollars)

And you thought alien sightings were the only interesting thing happening in Roswell, New Mexico! In 2007, a local car dealership came up with a brilliant plan to stimulate sluggish sales: mail out 50,000 scratch tickets, one of which would reveal a $1000 cash prize. But Atlanta-based Force Events Direct Marketing Company mistakenly upped the ante when they printed said scratch tickets, making every one of them a grand-prize winner, for a grand payout of $50 million. Unable to honor the debt, the dealership instead offered a $5 Walmart gift certificate for every winning ticket.

8. NYC DEPARTMENT OF EDUCATION’S LESSON IN BOOKKEEPING

The damage: $1.4 million

Humans and computers don’t always play well together. In 2006, New York City comptroller William Thompson admitted that a typo—an extra letter, to be precise—caused its accounting software to misinterpret a document, leading the city’s Department of Education to double its transportation spending (shelling out $2.8 million instead of $1.4 million).

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9. NYC MTA’S LESSON IN PROOFREADING

The damage: $500,000

Not to be outdone, just last month, New York City’s Transportation Authority had to recall 160,000 maps and posters that announced the recent hike for the minimum amount put on pay-per-ride cards from $4.50 to $5.00. The problem? A typographical error that listed the “new” price as $4.50. Oops! Of course, it will only take 100,000 rides on the 6 train to make up the difference. So straphangers lose (yet again).

10. AN EXOTIC VACATION BECOMES X-RATED

The damage: $10 million (plus $230 per month)

Remember the Yellow Pages? Yeah, well Banner Travel Services would like to forget them. Years ago, the now-shuttered Sonoma, California-based travel agency decided to market its services in the phone book ... only to find that the final printing advertised its specialization in exotic destinations as a forte in “erotic” destinations. The typo certainly piqued the interest of some new customers, just not the kind of clientele the company was hoping to attract. The printer offered to waive its $230 monthly listing fee, but Banner sued for $10 million anyway.

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Primary image courtesy of KABC.