Los Angeles (CNN) -- Orange is the new Brown wardrobe. Chris Brown's lawyer was unable to persuade a Los Angeles judge to let the singer out of jail on Monday.
Brown, 24, wore an orange jail jumpsuit at court, with his mother sitting behind him, while attorney Mark Geragos argued the singer should be allowed to enter another rehab program instead of spending the next month in jail.
The singer was locked up on a probation violation warrant Friday after he was booted from a court-ordered drug rehab program.
Assistant District Attorney Mary Murray said Brown has already been ejected from two rehab programs in the last five months and another program should not be considered.
Los Angeles County Superior Court Judge James Brandlin said he was concerned about a "provocative" statement counselors said Brown wrote on a card at the Malibu rehab center. "I am good at using guns and knives," according to a document read in court.
The rehab program told Brown to leave because of that statement and two other rules violations, the document said. Brown refused a drug test -- which his lawyer denied -- and he touched elbows with a female patient, according to the document.
Brown's next chance to get out of jail comes on April 23 when Brandlin considers if his arrest on a misdemeanor assault charge in Washington justifies keeping him locked up. There is a possibility the judge will speed up that decision so Brown can travel to D.C. for a trial on that charge.
Brown's legal troubles began five years ago, when he beat Rihanna as the two sat in a rented Lamborghini on a Hollywood street. He pleaded guilty to felony assault in June 2009, which resulted in a sentence of five years of probation and 1,400 hours of community labor.
The judge has revoked Brown's probation twice in the past year, most recently because of his arrest on a sidewalk near the White House after he allegedly punched a man.
Brown voluntarily entered a rehab program a day after being released from a Washington jail in October, but he was kicked out a few days later for "throwing a rock through his mother's car window" after a family session at the center, a probation report said. Brown was upset because his mother said she wanted him to stay in treatment, the report said.
"Mr. Brown proceeded to walk outside and pick up a rock and threw it through his mother's car window and it shattered," according to a letter from the rehab center included in the probation report.
His probation was revoked in November, but the judge allowed him to stay out of jail by entering a 90-day anger management and drug rehab program. Although he completed that program last month, the judge had ordered him to remain a resident at the Malibu treatment facility until a hearing on April 23.
Brown's probation officer reported at a hearing last month that the singer "continues to make great improvement" in dealing with anger, stress and drugs, but the judge decided he could not go free until after his trial for the assault charge in Washington on April 17. If he is convicted in that case, the judge would decide April 23 whether Brown should complete his probation in jail.
Brown has been working on a highway cleanup labor crew in Los Angeles three days a week to fulfill the 750 hours of service remaining in his probation requirements, his probation report said. At that rate, Brown could complete the labor in mid-October and possibly be free from probation requirements by the end of the year. However, the clock is stopped while Brown is locked up.
CNN's Topher Gauk-Roger and Carolyn Sung contributed to this report.