But there was nothing but smiles from the contented actress this week as a judge praised her for sticking to the strict new terms of her probation.
Superior Court Judge Stephanie Sautner said the Mean Girls star was doing well and urged her to keep up the good work.
The actress has completed 12 days at the county morgue and five therapy sessions since November 2, when she was sentenced to a strict routine of community service and counselling after her latest probation violation.
"You're doing well and I'd like to see it continue," the judge said during a ten-minute status hearing.
She also offered Lindsay an incentive to succeed, saying the actress could take leisure trips outside California after she completes a dozen days of morgue work a month.
The actress had permission from her probation officer to take a trip to Hawaii to celebrate her sister's birthday. She returned just hours before the hearing.
The 25-year-old has drawn the repeated ire of judges for failing to complete counselling sessions and community service assignments on time.
Judge Sautner made clear that she believes Lindsay's new schedule - which requires the model and actress to appear in court monthly until March - is the reason for the turnaround.
The judge even hinted that the star might end her supervised probation early if she works harder.
"Do more days a month and we can end this in February, possibly," judge Sautner said.