Cindy entered a powered armor competition on the planet Shirow; the same one Roland attended, and was the other final contestant in the last elimination.
Following the custom of the competition, and because she was dead broke and desperately needed a break, she made a side bet with her opponent Roland to bet everything they both owned on the final round- including their own freedom.
Roland won the final round, and claimed Cindy as his prize along with the purse and other winnings. Cindy was not happy with this turn of events, but kept her word and did not fight her situation.
Though displaying a badger's stubborn attitude, she eventually came around and fell deeply in love with her master Roland and became satisfied with her position and new life. This change in perspective came after the mutiny of the pirate fleet in which she along with most of the regular characters were taken as captives by the muntineers, and she found out the hard way that Roland had been far nicer to her than was typical for owners to treat slaves in the TT universe.