Grace Kelley, the daughter of country music star Wynonna Judd, asked a Virginia judge for something highly unusual as the birth of her second child approached.

She wanted to temporarily leave jail.

Kelley, 30, was serving a 15-month sentence when her attorneys filed a motion explaining that she was pregnant and expected to deliver her second child by scheduled C-section around Aug. 16.

Her legal team asked that she be released for approximately three days so the procedure could take place outside the jail environment, arguing that the arrangement would allow the delivery to occur in a sterile operating room and permit the baby’s father and other relatives to be present.

The request did not succeed.

A judge denied the motion during a July hearing, meaning Kelley would remain in custody as her expected delivery date approached.

The decision adds another complicated chapter to years of legal troubles for Kelley — and to a family situation in which her famous mother is already raising Kelley’s first child.

Kelley Was Serving a 15-Month Sentence

According to legal documents obtained by PEOPLE, Kelley had been held at Rockingham County Jail in Harrisonburg, Virginia, since June 18.

She was serving a 15-month sentence after pleading guilty to a misdemeanor charge of driving with a suspended or revoked license connected to an October 2025 arrest.

Then, on July 2, her attorney filed a motion revealing another major development.

Kelley was pregnant.

The filing said her second child was expected around Aug. 16 and that doctors planned to deliver the baby by C-section.

Her lawyer therefore asked the court to allow Kelley a brief temporary release.

The proposed arrangement was highly specific.

Kelley would be required to remain confined to bed for three days while undergoing the delivery and beginning her recovery.

Her attorney argued that denying the request would create complications surrounding the birth.

Her Lawyer Wanted the Baby’s Father to Be There

The motion did not focus only on Kelley’s medical needs.

Her attorney also raised concerns about what remaining incarcerated would mean for the baby’s father and other members of the family.

According to the filing, keeping Kelley in custody could prevent the child’s father from attending the birth.

It could also restrict relatives from visiting Kelley before and after the delivery.

The lawyer argued that the C-section needed to take place in an appropriate sterile operating room and presented temporary release as a way to accommodate both the medical procedure and family access.

But Judge Clark A. Ritchie was not persuaded.

The request was considered during a July 16 hearing.

Kelley participated virtually while remaining in custody.

The judge denied the motion.

PEOPLE reported that it contacted Kelley’s attorney for additional comment.

The published court details did not state whether Kelley subsequently delivered the child or provide information about the baby after the anticipated August birth date.

This Is Kelley’s Second Pregnancy While Incarcerated

The situation is particularly notable because Kelley was also incarcerated during part of her first pregnancy.

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

At the time, Kelley was serving time related to a probation violation that stemmed from a 2016 drug-possession case.

Today, Kaliyah is being raised by Kelley’s mother, Wynonna Judd.

Wynonna has spoken publicly about becoming a full-time caregiver to her granddaughter.

During a January 2025 appearance on Today with Jenna & Friends, the country singer described being with Kaliyah “24/7” and reflected on how raising her granddaughter had changed her life following the 2022 death of her own mother, Naomi Judd.

For Wynonna, becoming a grandmother raising a young child arrived during one of the most emotionally difficult periods her family had experienced.

Kelley, meanwhile, has said that her relationship with both her mother and daughter has become extremely complicated.

Kelley Said She Had Not Seen Her First Child in Years

In an August 2025 interview with PEOPLE, Kelley said she was sober and described herself as healthy and “at peace.”

But she also claimed that Wynonna had a restraining order protecting both herself and Kaliyah.

According to Kelley, that meant she was unable to communicate with her daughter.

She said at the time that it had been “a couple of years” since she had last seen Kaliyah.

That history makes Kelley’s second pregnancy particularly complicated.

The request for temporary release was not occurring in isolation.

It came after years of arrests, incarceration, addiction struggles and strained family relationships that had already resulted in Wynonna taking responsibility for Kelley’s first child.

Her Legal Troubles Stretch Back Years

Kelley’s encounters with the criminal justice system have been widely documented.

In 2018, she received an eight-year prison sentence after leaving a court-mandated drug recovery program, which violated probation connected to a 2016 methamphetamine possession arrest.

She was released early in December 2022.

But that did not end her legal problems.

Kelley returned to custody for several months in 2023 after violating parole and breaching a restraining order.

In April 2024, she was arrested in Alabama on charges that included indecent exposure, soliciting prostitution and obstructing governmental operations.

The prostitution-related charge was later dropped, while the indecent exposure accusation was reduced to public lewdness.

Kelley eventually pleaded guilty to public lewdness and obstructing governmental operations.

Later that year came another arrest involving allegations that she attempted to flee police while driving with a suspended or revoked license.

Then Came the Stolen Church Van Case

Another highly publicized incident occurred in October 2024.

Kelley was arrested after a van belonging to Ground Zero Church of the Nazarene in Charlottesville, Virginia, was stolen.

She initially faced multiple charges, including felony grand larceny.

The case eventually ended with reduced charges through a plea agreement, and she served six weeks in jail.

Kelley later spoke publicly about what had happened.

She said she had been hallucinating after taking what she described as “bad drugs.”

By August 2025, Kelley was describing a very different picture of herself.

She said she had achieved sobriety and wanted to move forward.

But another driving case eventually returned her to custody.

And by summer 2026, she was facing the prospect of giving birth to her second child while still serving her sentence.

A Famous Family Facing a Very Private Crisis

Grace Kelley’s story inevitably attracts attention because of her mother.

Wynonna Judd has spent decades as one of country music’s best-known voices, first alongside Naomi Judd in The Judds and later through her solo career.

But the latest court documents reveal a situation that has little to do with celebrity.

It is about an incarcerated woman approaching a C-section.

A lawyer asking a judge for three days outside jail.

A father hoping to be present.

A grandmother already raising another child.

And a family whose relationships have been repeatedly reshaped by addiction, arrests and incarceration.

Kelley’s attorney argued that temporary release would allow her second child to enter the world under more conventional circumstances.

The judge decided otherwise.

So as Kelley’s scheduled August delivery approached, the unusual request had a very simple legal outcome:

She had asked to leave jail briefly to give birth.

The court said she had to stay.