Wynonna Judd’s Pregnant Daughter Denied Temporary Release to Give Birth Behind Bars
Wynonna Judd’s daughter Grace Pauline Kelley asked a judge for just a few days outside of jail so she could give birth surrounded by family.
The judge said no.
Kelley, 30, is currently serving a 15-month sentence at the Rockingham County Jail in Harrisonburg, Virginia, and court documents reveal that she sought a temporary furlough ahead of the scheduled birth of her second child.
Her attorney filed the request on July 2, asking that Kelley be released for approximately three days surrounding a planned C-section expected on or about August 16.
The filing argued that temporarily releasing Kelley could make the delivery safer and allow the baby’s father and other family members to be present before and after the birth.
Her attorney also noted that keeping Kelley in custody would require sheriff’s deputies to remain at the hospital while she delivered.
The request reportedly had support from a captain with the Rockingham County Sheriff’s Office, but Judge Clark A. Ritchie still denied the furlough during a July 16 hearing, which Kelley attended virtually from jail.
That ruling did not mean Kelley would be forced to undergo the C-section inside the jail itself. Instead, authorities planned to transport her from the jail to a hospital for the procedure while keeping her in custody.
She Was Allowed Out to Give Birth the First Time
This is not the first time Kelley has been pregnant while incarcerated. When Kelley was expecting her first child in 2022, she was reportedly granted temporary leave from custody to give birth.
Her daughter, Kaliyah, is now 4 and has been living with her grandmother, Wynonna Judd, who reportedly has custody of the child.
The documents also shed light on Kelley’s reportedly strained relationship with her famous family.
According to reporting on the filing, Kelley said she had no contact or support from her biological family in Tennessee and specifically referenced her mother.
Kelley previously told People in 2025 that a restraining order prevented her from contacting both Wynonna and Kaliyah and that she had not seen her daughter in several years.
Meanwhile, Judd has openly discussed raising Kaliyah at her Tennessee home.
During a January 2025 appearance on Today With Jenna & Friends, the country singer spoke about life with her granddaughter on the family farm and the much different role she has taken on away from touring.
Kelley began serving her current sentence on June 18 after pleading guilty in a case involving driving with a suspended or revoked license following an October 2025 arrest.
She has faced a lengthy series of legal problems over the years, including a prison sentence tied to a probation violation in a drug case and multiple arrests following her release.
Kelley’s expected release date as November 16, 2026, after which she is expected to serve five years of supervised probation.