Court documents exclusively obtained by Us reveal that Wynonna Judd‘s daughter, Grace Pauline Kelley, has been denied a temporary prison release to give birth to her second child.

On July 16, a judge denied Kelley’s motion for a temporary furlough. The 30-year-old is currently serving a sentence of one year and three months at the Rockingham County Jail in Harrisonburg, Virginia, after she entered a guilty plea to a felony charge of driving with a suspended or revoked license on June 18, 2026.

Court documents obtained by Us show that Kelley’s legal team requested the temporary release on July 2, noting that she is expecting a baby “on or about August 16.” Her attorney requested she be allowed out for the delivery, but the judge ruled she must remain in custody. The documents state that Rockingham County Sheriff’s Office will escort her to the hospital for a scheduled cesarean section.

Kelley is already a mother to daughter Kaliyah Grace, who was born while she was on a leave of absence from jail in 2022.

Wynonna Judd’s Daughter Grace Kelley’s Ups and Downs Over the Years

Kaliyah has lived with her famous grandmother, 62, on her Tennessee farm for several years amid Kelley’s legal troubles.

The court documents reveal that Kelley has “no contact with her biological family in Tennessee” and receives “no contact or support from that side of the family,” specifically naming “biological mother [Wynonna Judd].”

Online records show she’s expected to be released on November 16 when she’ll be under supervised probation for five years.

In January 2025, the “Love Can Build a Bridge” singer opened up about being the caretaker of her granddaughter: “I don’t have a computer. I don’t watch television unless it’s planned ‘cause I’m raising my 2 ½-year-old granddaughter,” Judd shared on the January 30 episode of Today With Jenna & Friends. “I listen to her, so I don’t really do a lot of Instagram.”

The country superstar revealed her ideal day is centered around “food, family and fun.”

“My life on the farm is simple and sweet, which is what we need more of, I think,” she gushed to Today‘s Jenna Bush Hager. “We don’t do phones at dinner. … I do what I have to do to learn how to just live off the road ‘cause I was on the road at 17. So, I never got to learn how to do life outside of show business. So, now I’m learning.”

In August 2025, Kelley made shocking allegations, claiming her chart-topping mom knew she was being abused by her ex-stepfather, D.R. Roach.

Kelley told The Daily Progress that Roach, who was married to Judd from 2003 to 2007, allegedly molested her when she was 10 years old. She further claimed that the country singer chose not to initially expose him.

“When they found out in counseling what he had done to me, they’re like, ‘Wait a minute. We’re going to report this to law enforcement,'” Kelley claimed of her alleged abuse at the hands of Roach, seemingly referring to the counselors who are in most circumstances bound by law to report a crime.

Kelley continued, “When he was arrested and it came out in the news, that’s when she divorced him.” (Judd shares Grace and son Elijah Kelley with first husband Arch Kelley III.)

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Grace claimed that once Roach was arrested and charged in March 2007 with sexual battery against a minor, Judd tried to unite the family through counseling.

“So is my mom rich? Yeah, she’s so rich that she was able to sweep me under the rug and abuse me and then cover it all up,” Grace alleged. “I don’t want to talk bad about my mom, but we’ll just say she’s a good performer. She was never a mother.”

Judd’s troubled daughter has spent much of the past decade in and out of jail on various charges.

On September 5, 2025, Kelley was convicted of her second DUI in five years.

One month later, on October 27, police caught Kelley driving the wrong way down a street. According to court documents, Kelley admitted to driving erratically “probably because she had been drinking.”

Four days later, she was arrested at a CVS for reckless driving and shoplifting for allegedly stealing chargers and headphones, telling cops she “needed some things” but didn’t have money for them, according to records.

In October 2024, she was arrested for stealing a church van in Albemarle County, Virginia. Kelley spent six weeks in jail for the incident, revealing she had been hallucinating on “bad drugs” at the time.

In April 2024, she was charged with public lewdness and prostitution solicitation in Alabama.

Prior to that, Kelley was sentenced to eight years in prison in 2018 for leaving a court-mandated drug recovery program, which stemmed from a 2016 methamphetamine possession arrest.

In February 2020, Judd acknowledged the struggles in her daughter’s life during an interview on The Pursuit! with John Rich, calling Kelley “the strongest Judd woman in our ‘herstory.’ She’s healthier than I was at 23. How she got there – I would not go that way, but I was also sequestered. I was on a bus with my mother. Kind of hard to get in trouble. So that could have been me, John, if I didn’t have music.”