R&B singer Toni Braxton no longer holds the rights to 27 of her songs including"You're Making Me High," "How Many Wars," and "Always" after losing them in a bidding war. 

The Six-time Grammy award winner filed for bankruptcy in 2010 claiming debts as high as $50 million, according to TMZ. 

TMZ reports that after settling debts of $150,000 the singer was allowed to purchase the copyright to more than two dozen of her songs for $20,000 when put up for sale earlier this month.

However, Ross M. Klein doubled the singer's offer and swept the music catalogue out from underneath her.

Klein can now profit from those tracks.

Braxton still owns the rights to her most famous hit, "Un-Break My Heart."

This isn't the first time the 45-year-old singer has run into trouble.

Braxton previously filed for bankruptcy in 1998 for debts of $3.9 million. This year, debtors tried to collect $754,000 in fees earned for overseas performances.

This news comes less than a week after Braxton officially ended her 12-year marriage to Keri Lewis.

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