Wynonna Judd’s Daughter Grace Kelley Denied Temporary Jail Release to Give Birth to Her Second Child

Grace Kelley in August 2024.

Wynonna Judd’s daughter Grace Kelley will not be temporarily released from jail to deliver her second child after a judge denied a request filed by her legal team.

According to court documents obtained by PEOPLE, Kelley has been serving a 15-month sentence at Rockingham County Jail in Harrisonburg, Virginia, since June 18. She pleaded guilty to a misdemeanor charge of driving with a suspended or revoked license following an October 2025 arrest.

Her legal team filed a motion on July 2 asking the court to allow Kelley to leave custody temporarily so she could give birth outside the jail setting.

The filing revealed that Kelley was pregnant with her second child and expected to deliver around August 16 by scheduled cesarean section.

Her attorney argued that the planned C-section would require Kelley to remain “confined to bed” for approximately three days and that allowing her temporary release would make the medical process safer and less complicated.

According to the motion, Kelley’s lawyer claimed that refusing the request could “complicate the delivery of the child, which must be performed in a sterile operating room.”

The attorney also argued that keeping Kelley in custody could prevent the baby’s father from being present at the birth and limit the ability of family members to visit Kelley before and after the delivery.

Despite those arguments, Judge Clark A. Ritchie denied the request during a July 16 hearing.

Kelley participated in the proceeding virtually from jail, according to the legal documents.

PEOPLE reported that it reached out to Kelley’s attorney for comment.

The pregnancy marks Kelley’s second time expecting a child while dealing with incarceration.

She is already the mother of a daughter, Kaliyah, who was born in March 2022.

At the time of that pregnancy, Kelley was also incarcerated after violating probation connected to a 2016 drug possession case.

Today, Kaliyah is in the custody of Kelley’s mother, country music star Wynonna Judd.

Wynonna has spoken publicly about the experience of raising her granddaughter.

In January 2025, during an appearance on Today with Jenna & Friends, the singer reflected on caring for Kaliyah full time following the death of her own mother, country music legend Naomi Judd.

Naomi died by suicide at age 76 on April 30, 2022.

Wynonna explained that becoming deeply involved in her granddaughter’s daily life had changed her perspective during a period marked by grief.

“This past year, I’ve learned so much about myself, and now that I’m with my grandbaby 24/7, I’m learning that there is life after death,” she said at the time.

Grace Kelley’s current incarceration is the latest development in a lengthy history of legal problems stretching back nearly a decade.

In 2016, Kelley was arrested on a methamphetamine possession charge.

Two years later, in 2018, she was sentenced to eight years in prison after leaving a court-mandated drug recovery program, which constituted a violation of her probation.

She ultimately did not serve the entire sentence.

According to The Daily Beast, Kelley was released early in December 2022.

However, her legal difficulties continued.

She returned to prison between May and October 2023 after violating parole and breaching a restraining order.

In April 2024, Kelley was arrested again.

At that time, she was booked on charges that included indecent exposure, soliciting prostitution and obstructing governmental operations.

The case was later reduced.

According to The Daily News, the soliciting prostitution charge was dropped, while the indecent exposure allegation was reduced to public lewdness.

Kelley eventually pleaded guilty to public lewdness and obstructing governmental operations, according to Alabama news outlet WSFA.

She was ordered to pay $200 in connection with the public lewdness charge, while a 90-day jail sentence tied to that count was suspended.

For the obstruction charge, Kelley spent approximately 60 days in jail before being released on May 23.

Only a few months later, she was arrested again.

In August 2024, Kelley was accused of fleeing or attempting to elude a police officer.

She also faced charges of driving with a suspended or revoked license and improperly using motorcycle equipment.

According to an arrest record obtained by PEOPLE, Kelley was released after one day in custody on a $2,750 bond.

Her legal issues continued in October 2024.

That month, Kelley was arrested in connection with the theft of a van belonging to Ground Zero Church of the Nazarene in Charlottesville, Virginia.

According to the Albemarle County Police Department, Kelley initially faced several serious charges, including three counts of felony grand larceny.

She was also charged with driving without a license, destruction of property with intent, failure to use headlights and setting a vehicle in motion with the intent to commit a crime.

The case was eventually resolved through a plea agreement.

According to The Daily Progress, the charges were reduced to possession of drug paraphernalia, driving while under the influence of drugs and petty larceny.

Kelley ultimately spent approximately six weeks in jail.

She later spoke publicly about the incident and described being severely impaired at the time.

Kelley told The Daily Progress that she had been “hallucinating” because of what she described as “bad drugs.”

By August 2025, however, Kelley said her life had changed significantly.

In an interview with PEOPLE that month, she described herself as healthy, sober and “at peace.”

Wynonna Judd and Grace Kelley in March 2005.

She also addressed the fractured relationship between herself and Wynonna.

According to Kelley, Wynonna had obtained a restraining order that covered both herself and Kaliyah.

Kelley claimed that the order prevented her from communicating with her daughter.

She also said it had been “a couple of years” since she had last been able to see Kaliyah.

Those comments highlighted the ongoing family tension surrounding Kelley’s repeated legal troubles and her separation from her first child.

Now, less than a year later, Kelley is again incarcerated while preparing to become a mother for the second time.

The July motion filed by her attorney attempted to secure a brief period outside jail so she could undergo her scheduled C-section with the child’s father and other relatives able to be involved.

But the court declined to approve that arrangement.

As a result, Kelley remained in custody as her expected August delivery date approached.

The situation adds another complicated chapter to the long-running story surrounding Kelley, whose struggles with substance use, criminal charges, incarceration and family estrangement have repeatedly placed her in the public eye.

For Wynonna, it also brings renewed attention to a difficult family dynamic she has occasionally discussed while raising Kelley’s first daughter.

Although Kelley said in 2025 that she had reached a healthier and more peaceful place, her subsequent arrest and 15-month sentence have once again separated her from her family at a particularly significant moment.

With her request for temporary release denied, the birth of Kelley’s second child is set to unfold while she remains under correctional custody.