Making mistakes is a normal part of the human experience since there’s no one who gets everything right on the first try. But some mistakes come with a hefty price tag with lots of digits. They say there’s no point in crying over spilled milk, but losing thousands, even millions of dollars seems like a sensible reason to do so. Like these five errors below which ended up being some of the most expensive typos in history.

1. The $10 Million Yellow Pages Typo

For the owners of the Banner Travel Agency, their livelihood was turned upside down after the Pacific Bell, a telephone company, accidentally printed the word “erotic” instead of exotic. Apparently, this particular travel agency is one that provided exotic vacations but this simple error sent everything crashing down. They were forced to start from scratch after losing the majority of their customers, and also had to deal with a series of lewd phone calls. In the end, the business owner took action against the telephone directory by filing a $10 million suit.

2. The Organic Kitty Litter Nuclear Waste Explosion

So it turns out that inorganic kitty litter is a great way to store nuclear waste before chucking it away. But it absolutely has to be inorganic clay litter, otherwise there would be serious consequences. This was seen in 2014, when a drum of nuclear waste in New Mexico spilled everywhere. The culprit? Someone accidentally ordered organic litter after misreading hand-written notes. Organic litter can’t be used because it’s made from wheat, which is a cellulose that burns. Now combine that with nuclear waste and your pretty much have a ticking time bomb that cost an estimated $2 billion to cleanup.

3. The Billion Dollar Heist Typo

In 2016, a group of hackers began stealing credentials from the Bangladesh Central Bank, then sent transfer requests to take money from the U.S. Federal Reserve where Bangladesh holds a huge chunk of money. From there, nearly $81 million was sent to some random accounts in the Philippines and Sri Lanka. But the next transfer of $20 million was supposed to go to “Shalika Foundation” but was mistyped as “Shalika Fandation.” This error flagged the bank’s system and the transaction was automatically canceled. And of the $81 million stolen, only a small portion was recovered.

4. The Typo That Killed a 124-Year-Old Business

Taylor and Sons Ltd. was a Welsh engineering company who had been around since 1875. But all that came to an end in 2009, when the government listed them as out of business and in liquidation, leading to creditors, suppliers and customers quickly pulling out. Though everything was perfectly fine, and it was Taylor and Son Ltd, with a single son, not plural, who no longer existed. Even though the mistake was fixed within three days, it was far too late—the damage was already done. So after suing the government, they were awarded $17.2 million, which was collected over four years.

5. The Hurricane Harvey Insurance Payout

When the category 4 hurricane Harvey hit Texas and Louisiana in 2017, many people lost their lives, homes and businesses alike. And like anyone with insurance, a Texas bait shop owner expected to be compensated—in her case she had a claim for $60,000. But the insurance company refused to do so, all because the client’s agent mistyped her address as “1590 Hwy 361” instead of “1950 Hwy 361.” The insurer, Texas Windstorm Insurance Association wouldn’t fix the error but reversed their decision several months later after the story went viral.