The actress was taken into custody and escorted from a hearing after Superior Court Judge Stephanie Sautner revoked her probation because she was ousted from a community service assignment at a women's shelter.
"There has been violation after violation," Sautner said.
Bail was set at $100,000, and Lohan's spokesman Steve Honig said it was immediately posted. It was unclear, however, if Lohan had been released.
"We're dealing with someone on probation," said Lohan's attorney, Shawn Holley. "Most people on probation don't always do things perfectly."
A city prosecutor recommended jail time, but Sautner set a Nov. 2 hearing to decide whether Lohan should serve another stint behind bars, where she has been sent four previous times only to be released early due to jail overcrowding.
"If jail meant something in the state of California now, maybe I'd put her in jail," Sautner said.
The development marked the latest legal problem for the 25-year-old Lohan, who was given probation for a 2007 drunken driving case and a misdemeanor theft case this year.
"Lindsay is hoping this matter will be resolved on Nov. 2 and the court will reinstate probation and allow her to continue fulfilling her community service," Honig said.
Lohan had been ordered in April to serve 360 hours at the Downtown Women's Center, an agency that helps homeless women. Nine of Lohan's appointments at the center were "just blown off" and she "showed up once and left after an hour," Sautner said.
Lohan has since started serving hours with the American Red Cross, but Sautner said that would not count because it was not part of her sentence.
During the tense proceedings, Sautner hammered Lohan for failing to show up for her four-hour appointments at the women's center and taking six months to complete a court-ordered Shoplifters Anonymous course. The judge also questioned how Lohan could have complied with her court-ordered weekly psychological counseling when she was traveling in Europe from Sept. 9 to Oct. 5.
"I don't know how she did that in person every week," said Sautner, who suggested Lohan complete a minimum of 16 hours of her community service at the county morgue before the Nov. 2 hearing, when Lohan's probation officer and other officials will testify about her efforts to complete her sentence.
Lohan, aside from a role in last year's film "Machete," has seen her acting career evaporate in recent years. She has been in perpetual trouble since May 2010.
Another judge determined she violated her probation in a 2007 drunken driving case and sentenced her to jail and rehab. She faltered after being released early from a rehab facility early and was sent to the Betty Ford Center, where she got in an altercation with a rehab worker who later sued.
Within weeks of her release from Betty Ford, Lohan was accused of taking a $2,500 necklace without permission from an upscale jewelry store near her home in the Venice neighborhood of Los Angeles.
Sautner determined the January incident constituted a probation violation, and Lohan was ordered to undergo psychological counseling and perform 480 hours of community service, with 120 hours to be spent at the morgue.
Lohan later pleaded no contest to a misdemeanor charge in the theft case and served 35 days of a four-month sentenced on house arrest.