Imagine this: you’re browsing flights when you stumble upon a business-class ticket from Toronto to Cyprus for just $39 aboard Italy’s Alitalia Airlines. Mamma mia, what a deal! Surely it’s a mistake. But then you remember the warm buongiorno you got the last time you flew Alitalia. You picture the flight attendants in their sleek Armani uniforms serving steaming spaghetti. Besides, you’ve always dreamed of visiting Cyprus. That’s the sort of fare you can’t refuse! So you roll the dice and click “buy.”

You wouldn’t have been the only one to scoop the round-the-world bargain. But olive it was too good to be true. In 2006, Italy’s Alitalia Airlines accidentally listed this fare for $39 instead of $3,900. Within hours, over 2,000 people snapped up tickets–faster than you can say holy cannoli. When Alitalia realized their error, they tried to cancel the bookings. That didn’t fly and customers got saucy.

Faced with a PR nightmare, Alitalia waved the white flag, honoring the fare. It cost the airline a whopping $7.2 million. It ranks among the most expensive typos in history. But hey, at least those passengers got their pizza the action–traveling across the world in style for less than the price of Ciao-ing down on a nice dinner in Rome.

The typo left Alitalia’s finances between a rock and an al dente place. But it was far from the first meatball in the sauce.

Founded in 1947, Alitalia exploded onto the global stage in the 1960s during Italy’s economic boom. Its freccia alata, or “winged arrow,” was a symbol of national pride. The airline was the darling of the jet-set era, flying the Pope and showcasing Italian fashion, food, and elegance around the world. When you stepped onto an Alitalia flight, it was like stepping into a flying slice of Italy.

But the airline couldn’t keep up with the times. “The fall of Alitalia is the ultimate symbol of Italy’s historical, inbred difficulty in dealing with globalization and rising competition,” said Giovanni Orsina, director of the School of Government at LUISS University. Alitalia struggled to adapt to the rise of low-cost carriers and European deregulation. By the 1990s, the airline’s finances were crumbling faster than a biscotti forgotten in your espresso.

The government kept bailing Alitalia out, but as Orsina put it, “Authorities kept resuscitating it, believing that Alitalia just couldn’t fail, but there are limits, and we’ve reached the bottom.” It was like trying to patch a sinking Venetian gondola—doomed from the start.

Alitalia—finally pasta the point of no return—sold its last ticket in 2021. It was replaced by the more limited ITA Airways in October 2021. It was the end of an era for a once-iconic airline that had flown high on the wings of Italian pride, style, and class. But like a misprinted flight fare, some things just can’t last forever.