A recently single and broke Toni Braxton has lost the copyright to 27 of her favorite songs.

The six-time Grammy Award winner has filed for bankruptcy not once but twice.

The 45-year old R& B singer was given the opportunity to purchase the copyright of some of her best hits from her music catalog for $20,000 when they were put up for sale on July 15.

But Toni was unsuccessful in her bid to buy back ownership of some of her most famous hits – including You’re Making Me High and was outbid by another buyer TMZ reports.

Ross M. Klein doubled the low offer Braxton made and now he now owns the rights and can profit from hits like How Many Ways and Always.

But despite her gloomy predicament she still owns the rights to her most famous hit Unbreak My Heart, which was not included in the auction – for now.

Toni had previously filed for bankruptcy in 1998 for debts of $3.9 million and has legal trouble this year after her debtors tried to claim $754,000 in fees she made for International performances.