According to MTV News, Toni Braxton has filed for bankruptcy for the second time in her multiplatinum career.

The R&B singer, who has sold millions of albums and soared to fame with hits such as “Un-Break My Heart” and “He Wasn’t Man Enough,” recently filed for Chapter 7 bankruptcy in California, according to TMZ. Braxton reportedly insists she’s facing up to $50 million in debt and believes she may owe creditors such as American Express, AT&T, DirecTV, the Four Seasons Hotels, Neiman Marcus and the Westin. The singer asserts her financial worth lies between $1 million and $10 million.

Braxton has struggled with money woes in her career before. She famously filed for bankruptcy protection in 1998, after launching a lawsuit against her then-label, LaFace Records. She maintained that her recording deal was far below other top-selling artists and said she was earning 35 cents per album. (Fellow onetime LaFace artists TLC also took the record label to task in 1995 over a contract dispute and filed for bankruptcy at the height of their career.)

Braxton recovered from the financial fallout by embarking on a stint in Broadway’s “Beauty and the Beast” and the platinum 2000 release The Heat. She returned to the Great White Way in 2003 for “Aida” and released Libra in 2005, which debuted at #4 on the Billboard 200. Braxton also hoofed it on “Dancing With the Stars” in 2008 and released Pulse via Atlantic Records earlier this year. The album has yielded the singles “Yesterday” and “Make My Heart.”