Mario Anzuoni/Reuters/Landov
Kate Ward
October 21, 2011 AT 09:50 PM EDT

Lindsay Lohan is no stranger to jail. After all, the Mean Girls actress spent time behind bars several times between 2007 and 2010, thanks to a DUI arrest and several probation violations. (And that’s if you don’t count house arrest, which she was sentenced to serve earlier this year after being convicted of misdemeanor grand theft.) But following her latest setback — Lohan’s probation was revoked after she was let go from court-appointed volunteer work at the Downtown Women’s Center — media and fans alike are left wondering whether she’s set for another stint in the slammer, particularly after the actress was turned away from the L.A. County morgue Thursday for being late to court-ordered duty. After being given so many chances to improve her image, will the court finally turn its back on Lohan and send her directly to jail at her Nov. 2 hearing?

Though courts typically try to be lenient towards those serving probation, Lohan’s history certainly complicates matters for the actress, says Los Angeles-based criminal defense attorney Jonathan Kelman. Not only has she recently neglected to follow court orders, but she’s skipped DUI progress hearings and has failed drug tests in the past few years. (Her probation was previously revoked in 2010 after she admitted to failing a test.) “She’s making a mockery out of the system,” he tells EW. “She’s pushing so hard against the wall that eventually the court is going to push back….If you constantly keep mocking the court by not doing what you’re supposed to do, it’s a matter of time before she has to get sent to jail.”

In fact, by not sending her to jail already, the courts have been encouraging Lohan to begin walking on the straight and narrow path. If Lohan had previously been sentenced to an extended period of time in jail — instead of probation and community service — the courts wouldn’t have been able to monitor her health after she served time, says criminal defense attorney Robert Schwartz, who is also based out of Los Angeles. “What the judge is trying to do is squeeze out of her the community service, and actually help her by forcing her to get treatment,” says Schwartz. “At some point, [Judge Stephanie Sautner] is going to completely lose patience. Maybe she’s already reached that point.”

But if Judge Sautner — who oversaw Lohan’s misdemeanor grand theft conviction and probation — has lost patience and chooses to sentence the actress to jail time, how long can we expect Lohan to serve behind bars? Though, at maximum, she could be required to serve a year, overcrowding in the California jails could severely limit the actual number of days she spends in jail, says criminal defense attorney Gregory Caplan, also in Los Angeles. Most inmates incarcerated for misdemeanor or non-violent crimes at California’s Century Regional Detention Center only serve 10 percent of their full sentence. That makes it tough for officials to truly rehabilitate probation violators. “To some degree,” says Caplan, “it’s difficult for a judge to really send a message on misdemeanor cases.”

And Lohan could delay a jail sentence. Schwartz says the actress and her legal representation could appeal the judge’s decision, which would tie the case up in the appellate department of the L.A. Superior Court. “She could remain at liberty for a year,” he says, should she be sentenced to jail.

Still, it’s in Lohan’s best interest to avoid jail time, no matter how short or easy it is to appeal. “I don’t care what superstar you are, you never want to spend a minute in custody,” says Kelman. “Point is, she’s going to try to weasel out of any way of getting any type of jail time, and the only way she’s going to be able to do that  is [to] put up or shut up.”

So how can she put up? Simply by following through with probation orders from Judge Sautner. Though the morgue snafu definitely set her “off on the wrong footing with Judge Sautner,” she has the opportunity to prove to the courts that she’s taking her probation seriously. “Now, her showing up late [to the morgue], if that was her last shot to be there and she was due in court the following day, that would have been a horrific situation,” says Kelman. “But guess what? She’s got plenty of time to do it, so she’s going to go now and work it out. If she doesn’t have completed paperwork the next time she’s in front of Judge Sautner, she will end up going to jail.”

And though Lohan has to cope with the media chronicling her every move — or misfire — Lohan could use attention from news outlets to her benefit. “If she does things that she’s not asked to do, but does things that are incredibly beneficial to the community, that will look wonderful because the press will report it,” Kelman says. “She’ll come to court showing that she just showed up at the Beverly Hills high school to talk about how drinking and driving is bad. Things like that would be a benefit.”

Of course, even should Lohan improve her image before her Nov. 2 hearing, we can’t count out more stern words from Judge Sautner, who admonished Lohan and ordered that she be dismissed in handcuffs after revoking her probation Wednesday — especially after the media publicized her tardiness at the morgue the very next day. “I feel bad in a sense that she can’t do anything because the media is following her everywhere on everything,” Kelman says. “But I don’t feel bad because she has the ability to complete some of these things. All she has to do is get it done. If she gets it done, there isn’t a problem. But when you’re a superstar and you think you can drag your feet and do whatever you want, eventually it will catch up to you.”

Follow Kate on Twitter @KateWardEW

Read more:

Lindsay Lohan shows up for morgue duty, says rep

Lindsay Lohan gets lost reporting to morgue duty, but official says ‘she’s been here before’

Lindsay Lohan handcuffed at hearing, sees probation revoked

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