Wynonna Judd’s pregnant daughter Grace Kelley was denied temporary release from jail to give birth.
Kelley, 30, is currently serving a fifteen-month sentence at Rockingham County Jail in Harrisonburg, Virginia, after pleading guilty in June to a felony charge of driving with a suspended or revoked license. Her legal team filed a request for temporary furlough on July 2, but a judge rejected the petition two weeks later, according to a report that surfaced Wednesday. She is expecting the baby “on or about Aug. 16.”
Instead of being released, Kelley will be escorted by the Rockingham County Sheriff’s Office to the hospital for a scheduled cesarean section. It remains unclear whether the procedure has already taken place.
This marks a sharp contrast from Kelley’s previous pregnancy. She welcomed daughter Kaliyah in April 2022 while also incarcerated, but at that time she was granted a leave of absence from jail to give birth. That 4-year-old child now lives with Judd, 62, on the Grammy winner’s Tennessee farm.
Court documents from Kelley’s current case state she has “no contact with her biological family in Tennessee” and receives “no contact or support from that side of the family,” including her “biological mother.” The filings do not name Judd directly, though the singer has been publicly raising Kaliyah.
Kelley’s criminal history stretches back to 2015. She is scheduled for release on Nov. 16 and will then serve five years under supervised probation.
Judd has largely kept quiet about raising her granddaughter, though she offered a rare glimpse into their life together during a January 2025 interview on the “Today” show.
“Food, family and fun is my goal,” the “No One Else on Earth” singer said. She noted they “don’t do phones at dinner” and don’t “watch television unless it’s planned.”
“My life on the farm is simple and sweet, which is what we need more of, I think,” she added.
The denial of Kelley’s furlough request comes amid continued public interest in the Judd family’s private struggles. Naomi Judd, Wynonna’s mother and Kelley’s grandmother, died by suicide in April 2022, just weeks before Kaliyah’s birth. The family has since navigated both grief and the ongoing complications of Kelley’s legal issues.
Kelley’s most recent troubles include an arrest in April for soliciting prostitution and a subsequent warrant after fleeing police, according to prior reports. Her pattern of arrests has spanned nearly a decade across multiple charges.
Wynonna Judd’s representative did not immediately respond to requests for comment on Kelley’s current pregnancy and denied furlough.
In the viral moment that first drew widespread attention to Kelley’s situation, she was arrested in April on prostitution-related charges and later fled from police, triggering an additional warrant. That incident marked her second arrest since April and compounded her legal troubles ahead of the June plea that landed her the fifteen-month sentence she is now serving.
Kelley’s history with the justice system dates to 2015, with charges accumulating across multiple jurisdictions over the years. The current Virginia sentence represents one of her longer incarcerations, with the November release date now carrying the added complexity of a newborn child whose custody arrangements remain unreported.
Judd is scheduled to perform at the Iowa State Fair in Des Moines on August 10.