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. Last weekend, 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. Not only is the mega-search engine’s own name a happy accident (it was supposed to be Googol; the domain name was incorrectly registered), but Harvard University researchers claim that the company earns about $497 million each year from everyday 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.

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. Read More…