Rosie O’Donnell is opening up about her daughter Chelsea’s prison sentence, sharing a heartfelt message of support as the 28-year-old faces consequences for violating her probation in a drug-related case. The former talk show host took to Instagram this week to speak out, pairing her post with a photo of Chelsea from before addiction took hold.

“My child Chelsea Belle — before addiction consumed her life, I loved her. I love her now as she faces a scary future,” O’Donnell wrote, adding the hashtags #AddictionAwareness, #Love, and #Family. “Prayers welcomed.” In a separate statement to Us Weekly, which first reported the sentencing, O’Donnell expanded on her heartache: “I have compassion for those struggling with addiction — Chelsea was born into it, and this has been a painful journey for her and her children.” She emphasized, “We continue to love and support her through these horrible times. Prayers welcomed.”

Chelsea, who O’Donnell adopted as an infant with ex-partner Kelli Carpenter, is a mother of four: daughters Skylar Rose (2018), Riley (2021), and Avery Lynn (2022), and son Atlas (2023). Her legal troubles date back to late 2024, when she faced three back-to-back arrests: first in September on felony child neglect and drug possession charges, again in October for similar offenses, and a third time in November on felony counts related to methamphetamine and narcotic possession.

In March 2025, Chelsea struck a plea deal covering all three arrests, leading to a six-year probation sentence with strict terms: absolute sobriety, no contact with known drug users, completion of a high school diploma or GED, and a mental health evaluation. At the time, a Wisconsin judge sentenced her to 18 months in prison but stayed the term, allowing probation as long as she complied with the rules.

For a brief period, Chelsea showed signs of progress. In April 2025, O’Donnell shared on her Substack that her daughter had earned her high school diploma — a decade after dropping out — and that a Wisconsin judge had praised her for completing treatment. “She called me with so much energy, joy, and self-confidence,” O’Donnell wrote at the time. “‘Mom, I got my diploma. Ten years too late, but I got it.’ I cried quietly, remembering her school anxiety years ago. I’m so proud of her.”

But by fall 2025, things took a turn. Court records show Chelsea violated her probation, with a drug treatment court official citing sexual assault allegations (no further details were provided) and a lack of significant progress in her treatment program. The Marinette County Treatment Drug Court Team deemed the violations “sufficient grounds” to terminate her from the program.

The Marinette County Sheriff’s Office confirmed Chelsea has been in custody since September 9 and will soon be transferred to Taycheedah Correctional Institution, a medium-security prison in Wisconsin — though she may be moved to another facility to serve her sentence. Officials have not disclosed the length of her term.

Chelsea’s probation violations weren’t isolated: In April, she spent a few days in county jail for breaking court rules but retained her probation. June brought a hearing over a “medication violation” (she was ordered to write and recite the program’s medication policy) and a two-hour ditch-picking sentence for missing an appointment. By late July, she faced allegations of “dishonesty,” leading to a return to phase two of her treatment program and a required apology letter to her landlord. In September, she was sentenced to two weeks in county jail and told to write an essay explaining why she deserved a “last chance” instead of probation termination.

Through it all, O’Donnell has maintained her support, even as she acknowledged the complexity of Chelsea’s journey — including her daughter’s desire for privacy and past struggles with their relationship. “Her recovery, her journey is her own,” O’Donnell wrote on Substack earlier this year. “I’m proud of her for living her truth, and I respect her desires, her struggles, her successes.”

As Chelsea begins her prison sentence, O’Donnell’s message remains clear: love and solidarity in the face of adversity.