Earlier in the day his publicist Darryll Johnson told ABC7 the singer plans to pay more than $161,000 he owes in back child support so he can be released Friday afternoon. However, jail officials said he will be spending another night in jail as the money was never posted.
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Kelly returned to jail after he could not pay the money and was led away by deputies and handcuffed following a child support hearing Wednesday.
Kelly is being held in a solo cell under 24 hour observation, which is jail protocol for high-profile inmates, the Cook County Sheriff's Department said.
WATCH: R. Kelly leaves Trump Tower for court appearance
R. Kelly leaves Trump Tower for court appearance
Kelly is charged with 10 counts of criminal sexual abuse. Last month, the Cook County state's attorney said new allegations have surfaced, and at least three women claim, when they were minors, Kelly sexually assaulted them. Kelly pleaded not guilty to all charges.
After the charges were announced, R. Kelly voluntarily surrendered and spent a weekend in jail before a female acquaintance posted a $100,000 bond to get him out.
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TIMELINE: History of R. Kelly sex abuse allegations
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R. Kelly's next hearing on the sexual abuse charges is March 22.
In addition, Detroit police now looking into a separate allegation from 2001 with a 13-year-old girl.
READ: R. Kelly indictment documents
Attorney Gloria Allred said she represents the Detroit woman, and shared a comment from her client which reads: "...listening to R. Kelly's denials about what he did to underage girls like me was very hurtful. He needs to tell the truth and he needs to stop playing the victim. He was the adult and I was the child. He had no right to take advantage of me when I was only a 13 year old child."
Meanwhile, his girlfriends, 23-year-old Joycelyn Savage and 21-year-old Azriel Clary defended Kelly in an interview with CBS News. Both deny they've been brainwashed by Kelly and are now turning attention to their own parents.
"Both our parents are basically out here trying to get money and scam, because they didn't agree on what happened, you know, with music or whatever it could be and they're just very upset," Savage said.
WATCH: R. Kelly enters Chicago courtroom for child support hearing
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R. Kelly enters court for child support case
The women allege their families are exploiting their relationships with Kelly for money.
"My dad and my mom, they're starting to send threats to both me and him," Clary said. "They said I'll put all your naked pictures all over the world. I am going to ruin you and I am going to ruin him if he doesn't send $20,000 to this bank account by Monday or I am going to put everything out there then $10,000 after that."
Both sets of parents deny ever asking for money.
SEE INSIDE: R. Kelly's West Loop studio
SEE INSIDE: R. Kelly hasn't cleared bedroom from West Loop studio, inspectors say
The Grammy-winning artist has sold more than 40 million albums in his career.