That's the question a Beverly Hills judge is expected to address Friday when the actress faces a probation violation hearing for failing a drug test last month in her DUI case.
Lohan, 24, who's ordered to appear in person, has voluntarily spent the last three weeks at the Betty Ford Center in Rancho Mirage, Calif. – at least her fifth time in rehab – after she bailed out of jail on Sept. 24.
"The key here is her progress in treatment," says L.A. criminal defense attorney Steve Sitkoff, who's not involved in the case. "The better she's doing in rehab, the less likely Judge Elden Fox will throw her in jail."
Any number of scenarios could play out on Friday:
Lohan could be found in violation and be sent back to jail on the spot
The actress could be ordered to stay in rehab in lieu of jail
She might skip the hearing if her attorney can provide a letter from the Betty Ford Center demonstrating her progress
Judge Fox could postpone the hearing all together to see how well she does in treatment
"Judge Fox has to balance whether to help Lindsay with her addiction or punish her with jail," says Sitkoff. "But if she continues to mess up by not following the court's orders, he won't hesitate to lock her up."