Britain’s gambling authorities have ordered Caesars Entertainment to pay a record fine of $16 million for failing to prevent money laundering and for allowing people with gambling problems to lose huge amounts over repeated visits to its casinos.

The Gambling Commission said the British unit of the U.S. hotels and casinos company would have to pay 13 million pounds for racking up a “catalog” of failures over three years. Three senior managers also had to surrender their licenses to work in a casino.

The commission investigated Caesar’s 11 casinos throughout Britain and said it found systemic failings in the way the company dealt with high-spending, frequent customers.

Among the instances cited by the commission was a customer who had signed up for a program to be denied service at casinos, citing gambling problems, but was nonetheless allowed to go on to lose £240,000 over 13 months. Another, who displayed signs of problem gambling and had more than 30 sessions over five hours long, went on to lose £323,000 within a year at Caesars casinos.