Princess Eugenie and her family are likely in a state of bliss right now as news broke on Monday that the princess got engaged to her boyfriend of seven years, Jack Brooksbank. The couple became engaged earlier this month in Nicaragua and are planning to marry in the fall.

Unfortunately, good news isn’t something that has always surrounded the family in the past, since Princess Eugenie’s mother, Duchess of York Sarah Ferguson, has gotten herself into quite a bit of money troubles over the years, spanning all the way back to the 1990s.

The Duchess first found herself in debt after she divorced Prince Andrew, Princess Eugenie’s father, in 1996 and landed a settlement reportedly worth £3 million. Some of it was for her daughters and some was for herself, but she ended up spending more than she could afford and found herself owing money.

By 1998, though, she was able to dig her way out of the financial hole by becoming an ambassador for various companies, with her relationship with Weight Watchers being the most beneficial as she allegedly earned £2 million a year for her work.

Aside from Weight Watchers, she also received money to speak at events, appear at engagements and by signing on as spokesperson for Waterford Wedgewood, which earned her £500,000 for a one-year contract. All was good for a few years, until the wellness company she created, Hartmoor, fell into debt of over £600,000 in 2009 and she quickly found herself being pursued by three firms for bills she owed.

Money issues only continued from there and got so bad that her family had to step in to help her out of the £2 million debt she found herself in. Her ex-husband had his private office at Buckingham Palace figure out her finances and limit her spending in order to get it all back on track.

Hopefully, since a few years have passed, the Duchess of York and her family have been able to put all of her past monetary issues aside to properly celebrate Princess Eugenie’s engagement and to begin planning her wedding all together.