"It is something you will never forget," former inmate Tanya told "Good Morning America" today. "When you get strip searched it takes away a lot of dignity. You are not in a room by yourself."
But ABC News legal analyst Dana Cole said that for most of her time behind bars, Lohan will just be bored.
"It's not going to be the worst situation imaginable, far from it," Cole said, noting that she'll be separated from other inmates for her own protection. "It's just going to be boring basically."
At least Lohan will be cooped up with someone she knows -- sort of. The Los Angeles Times reported today that one of Lohan's inmates at the Lynwood jail is 19-year-old Alexis Neiers, whose "bling ring" of accused burglars targeted celebrity residences, including Lohan's Hollywood Hills home.
Neiers is currently serving a 180-day sentence for felony first-degree residential burglary of actor Orlando Bloom's home.
Of course, because Whitmore noted that Lohan "will be kept away from [the] general population" of the jail, they may not meet at all.
The days leading up to Lohan's surrender were anything but serene. According to People magazine, she spent a stressful weekend at the Pickford Lofts sober living facility in L.A.
"She has not been able to sleep and has barely been eating. All weekend, Lindsay kept crying, chain smoking and chewing her nails," a source told People. "She is a nervous, fidgety mess, and her legal team, family and friends are very concerned about her fragile state."
But the night before heading to court and then jail, Lohan seemed at least a little lighthearted. On Twitter, she wrote "the only "bookings" that i'm familiar with are Disney Films, never thought that i'd be "booking" into Jail... eeeks."
She also retweeted an ABCNews.com story about pets victimized by the BP oil spill.
Lohan is scheduled to be released from jail in time for the premiere of her newest movie, "Machete," in which she plays a gun-toting nun.
This will be Lohan's second time in jail. She spent 84 minutes in prison in 2007 after pleading guilty to two misdemeanor counts of being under the influence of cocaine and no contest to two counts of driving with a blood-alcohol level above 0.08 percent and one count of reckless driving.
The year 2007 was also the year of two very public arrests for Lohan. She was sentenced to three years of probation but requested a one-year extension in October after failing to complete her alcohol-education courses on time.
ABC News Radio's David Alpert contributed to this report.