Jelly Roll is not hesitant to return to jail; he does it to inspire inmates.

On Thursday, he made a visit to both Pendleton Correctional Facility and Pendleton Juvenile Correctional Facility.

This visit took place before his performance on November 7 for the Beautifully Broken tour at Gainbridge Fieldhouse in Indianapolis.

“He communicated his remarkable story of perseverance, providing encouragement and hope,” noted the Indiana Department of Corrections in a social media update regarding the visit. “His message remains a source of inspiration, proving that regardless of history, the future is ripe with possibilities.”

Earlier in October, Jelly Roll drove to a detention center in Kentucky to speak to participants of a men’s substance abuse program before performing in Louisville.

The 39-year-old artist from Nashville has openly shared his modest beginnings, previously working as a drug dealer and selling his mixtapes out of his car since 2003. After facing two criminal charges at 18, he repeatedly encountered jail time due to drug offenses until 2016.

He made his entrance into country music with the release of “Son of a Sinner,” which topped the Billboard charts in January 2023.

Jelly Roll has earned three CMT Music Awards and was recognized as the best new artist at the 2023 Grammy Awards. He also secured awards for video, male video, and performance of the year at the 2024 CMT Music Awards.

Recently, he was revealed as a nominee for the 2025 Grammy Awards in the categories of best country solo performance and best country song for his piece “I Am Not Okay.”

During his Indiana visit, Jelly Roll was accompanied by Ernest, who is the opening act for his tour.

Ernest, whose full name is Ernest Keith Smith, has also received a nomination for best country song at the 2025 Grammy Awards for “I Had Some Help,” which he co-authored.