Bobby Brown, who was arrested and jailed in Massachusetts on Sunday for failing to appear in court and pay child support fines, will remain behind bars until he pays $19,150, a judge ruled Monday.
Brown, 40, owes suport to his former girlfriend Kim Ward, who lives in Massachusetts and with whom he has two teenage children: LaPrincia and Bobby III.
The singer's attorney, Phaedra Parks, said she didn't expect Brown to get the money until Tuesday, and said he's been struggling to make the payments he owes to Ward.
"Although this agreement was put in place when he was Bobby Brown the star, this agreement is being enforced when he is not always able to find work," Parks told the Associated Press. "He hasn't made an album in quite some years."
Brown was also ordered to return to court on Thursday – the day when his next $5,500 support payment is due.
"Kim always finds these hearing to be extremely difficult," Ward's lawyer, Linda Medonis, said. "This is not the route she wants it to go, but when he doesn't pay for a few months it becomes a real hardship for her."
Brown was arrested Sunday evening outside his daughter's cheerleading competition, Patrick McDermott, clerk of Norfolk Probate Court in Canton, Mass., told PEOPLE. "He went very cooperatively," he says. "According to the constable, no one was really around."
Jerry Loomis, one of the constables who arrested Brown, said he stopped the singer in the parking lot "because we didn't want to embarrass him or anyone else in there."
Asked if Brown was able to see his daughter perform Loomis said, "No. He was begging us to go in there, but we felt for safety reasons we couldn't allow him. It wasn't even in the cards."
In October, a judge ordered Brown to be arrested
if he stepped foot in the state after the singer skipped a court hearing over $11,000 in delinquent child support payments to Ward.
Later that month, McDermott said that Brown had paid what he owed
to Ward; however, the arrest warrant has remained in place – probably in case Brown fell behind again, McDermott said.
Brown, who split from Whitney Houston
in September, has a history of missed child support payments, and was even jailed in March 2004 for one day after missing several payments, which he subsequently paid.