Chelsea, the daughter of well-known personality Rosie O’Donnell, is now facing a challenging future as she heads to prison following a decision by a Wisconsin judge to revoke her probation in October 2025.

At 28, Chelsea, a mother to four children, will serve her sentence due to significant breaches that disqualified her from the opportunity for rehabilitation via the drug court program.

Reasons for Chelsea O’Donnell’s Probation Revocation: Assault Allegations

Court documents reveal that the revocation of Chelsea’s probation stems from accusations of sexual assault, though officials have remained tight-lipped about the specific details surrounding the case.

The Marinette County Treatment Drug Court Team evaluated these allegations, coupled with Chelsea’s insufficient progress, and deemed them as “sufficient grounds for termination” from the program. These serious claims prompted the judge to enforce her previously stayed sentence, as confirmed by an official.

Explanation of Chelsea O’Donnell’s Incarceration

Chelsea’s legal troubles began with a series of arrests in 2024 on charges that included possession of methamphetamines, child neglect, and bail jumping. By January 2025, she had pleaded guilty and was sentenced to a six-year probation period, which came with strict conditions to maintain sobriety.

Despite these conditions, Chelsea committed several violations, including issues related to medication management, missed appointments, dishonesty, and suspensions from work, which led to her detention in September 2025. The court hearing on October 22 resulted in the activation of her previously stayed 18-month prison sentence.

Rosie O’Donnell’s daughter, Chelsea O’Donnell, is facing serious legal trouble again😳

New records detail allegations of sexual misconduct and probation violations that led to her jail sentence in Wisconsin.https://t.co/JVWgVqknBl

— The Blast (@TheBlastNews) February 25, 2026

Details on Chelsea O’Donnell’s Sexual Assault Allegation and Probation

The sexual assault claim was the tipping point in a long history of non-compliance. Chelsea’s probation mandated complete sobriety and active involvement in drug court programming, but officials reported that she did not make notable progress throughout 2025.

The treatment court team reviewed her situation and unanimously agreed on termination, prompting Judge James Morrison to revoke her probation and mandate her time at Taycheedah Correctional Institution.

Factors Leading to Chelsea O’Donnell’s 2025 Jail Sentence

A series of infractions throughout 2025 sealed Chelsea’s fate. She spent part of April in jail due to rule violations, encountered medication issues in June that required her to recite written policies, and received citations for dishonesty in July.

In August, she was required to perform community service due to work suspensions, while September led to a two-week jail sentence alongside an essay appealing for another chance. The court documented her challenges comprehensively before ultimately mandating termination from the drug court and activating her prison sentence.

Facts on the Probation Revocation of Rosie O’Donnell’s Daughter

Rosie O’Donnell has consistently expressed her support for her daughter through various legal challenges, recently posting a childhood image on Instagram with a request for prayers. The comedian, who relocated to Ireland earlier this year, told Us Weekly that her daughter is on a “difficult journey,” but the family remains loving and supportive.

Chelsea has been in custody since September 9 and will be transferred to a medium-security facility in Fond du Lac, Wisconsin, to serve her undisclosed sentence.