For the past seven years, Kelly, a mother of three from Illinois, has spent most of her time behind bars. She's one of 2 million incarcerated Americans.
Growing up, Kelly never imagined herself in the correctional system. "I had a good life growing up. I was a cheerleader in high school," she says. "I was on the honor roll." Then, Kelly says she started getting high and became addicted to heroin.
In 2002, Kelly was arrested for residential burglary and spent two years in prison. While in jail, she gave birth to a son, John, who was sent to live with her mother. Kelly was released in 2004, but her freedom was short-lived. In 2006, she says she tried to snatch a woman's purse to get money for drugs.
Kelly was convicted of attempted robbery and sent to the Lincoln Correctional Center in Lincoln, Illinois, for almost three years.
Oprah's cameras were there for the days leading up to Kelly's release, a frightening time for many inmates.
"The scariest thing about leaving tomorrow is for my best not to be good enough, for someone to not give me a chance," she says. "I could just imagine the pain that I've caused people. I really am truly sorry."
When the lights go out in the room she shares with drug dealers, burglars and murderers, Kelly says she thinks about the consequences of her actions.
"My mom can forgive me. My kids can forgive me. Everyone can forgive me," she says. "How am I going to forgive myself for everything that I've done, for all the hurt that I've caused everyone?"
In the early morning hours, Kelly walks out of prison for what she hopes is the last time. "I'm nervous. I'm excited," she says. "It's like a new beginning. It's a new day."
The odds of Kelly staying out of prison are not in her favor. According to statistics, almost 50 percent of women who are released from prison will be back behind bars within three years.
Kelly boards a train and begins the three-hour journey home, a place she hasn't been in 900 days. Her mother, Lorri, and the three children she left behind are waiting for her to return. Kelly's 4-year-old daughter, Janet, was born after her first incarceration, and her youngest son, Jackson, is just 2 years old. John is now 6 years old.
John, Janet and Jackson's grandmother Lorri has been their caretaker since they were babies. Kelly says she's anxious to form bonds with each child without correctional officers calling the shots.
"My kids aren't happy with me right now. I don't know what kind of food they like, their favorite colors," she says. "When I call on the phone, [John] doesn't want to talk. He doesn't think that I love him, because I'm not home."
Kelly says she appreciates the sacrifices her mother has had to make over the years. "My mom is my everything," she says. "She said, 'When you're in jail, I'm in jail.' So she's put her life on hold for me to help raise my kids."
Lorri says prison is not the dream she had for her daughter…but it's what she deserved. "I think it's been a learning experience for her," she says. "I think it's going to be a lot different this time. I'm just worried about her getting in with the wrong people and maybe being swayed."
When Kelly's train finally arrives at her stop, her mom and children rush out to greet her. "When she came off that train, it was probably the best feeling in the world," Lorri says. "It's hard when your loved one's away."
Janet and Jackson give their mom big hugs, though John is more hesitant. Despite the challenges she may face, Kelly says coming home to her family felt incredible. "I missed them. It was a chance to spend time with them without people around," she says. "They can run around. They can be themselves, and we can all play together. It's a great feeling."
Now that she's home, Kelly says she has to ease back into her children's lives. "The power struggle is there right now," she says. "I'll say no, and they'll run to [my mom]. … I'm trying to not be too overbearing with them right now, because I don't want them to think that I'm going to come in and just be the ruler."
Since she's been home, Kelly has set other goals for herself. She says she was accepted into beauty school and is trying to find a job. "Little steps at a time. If I don't get a job this week, I'll get a job next week," she says. "If I don't get one next week, there's always tomorrow."
Kelly says she knows there will be setbacks, but if she can learn from her mistakes, she'll be fine. She credits her strong support system for making this transition back into society easier than the last.
As additional motivation, Kelly knows that if she's convicted of another felony, she could spend a minimum of 14 years behind bars. If this happens, Lorri says she'll seek full custody of John, Janet and Jackson. "It's the last time, and then I take the kids," Lorri says. "I can't put the kids through it anymore. They don't deserve it."
Many of the women Kelly depends on for support and encouragement are still behind bars at the Lincoln Correctional Center. Joanna, an inmate serving 13 1/2 years for armed violence and conspiring to commit first-degree murder, says she believes in her friend.
"She's getting the opportunity to start her life again and help raise her kids. She's got the opportunity to make something of herself and put this place behind her," Joanna says. "She can just think about how hard it was in here and make the right decisions in life."
Jessie and Tina, two other inmates, also wish the best for Kelly and her family. "I just want her to remember, every day, to do the best that she can," Tina says.
Oprah says 700,000 people like Kelly are released from prison every year. "We need to do whatever we can to rehabilitate and have support services so that it doesn't happen again," she says.