Rosie O’Donnell posted to Instagram on Thursday a photo of her posing with her daughter Chelsea, who is currently serving a prison sentence, as she shared a text message they had.
The 64-year-old comedian, who guest hosted Jimmy Kimmel on his late night show last week while on summer vacation, stayed on point in her text exchange with 28-year-old Chelsea.
In an accompanying photo, which appeared to have been taken in June O’Donnell visited Chelsea in prisonRosie wore a black shirt, while Chelsea was dressed in a green button-up top, and both were smiling.
During the text exchange, Chelsea told her mother, “Thanks mom, I got my music back today.
‘How are you? I’m trying to reach the social worker to let her know about the plans for when I’m released. Hannah texted her for me.”
Rosie replied: ‘Okay, I’ve had my nails done – no more gel for me, my nails are ruined,’ before asking: ‘Are you reading a good book?’
Rosie O’Donnell, 64, posted to Instagram on Thursday a photo of her posing with her daughter Chelsea, 28, who is currently serving a prison sentence, as she shared a text message they had
Chelsea replied, “I’m reading the legacy series…it’s really good that she has a bunch of other books too.
‘And yes me [haven’t] I’ve been painting my nails for years, but I remember that stuff ruining my nails.’
The Daily Mail has contacted O’Donnell’s representatives for further comment on the story.
Chelsea is in the middle of an 18-month prison sentence she is serving at the Taycheedah Correctional Institution in Fond du Lac, Wisconsin.
She had been sentenced in October 2025 after multiple probation violations, coupled with guilty pleas from a string of arrests in 2024.
At the time of her arrests in 2024, Chelsea was in custody on charges including possession of methamphetamine and child neglect.
Chelsea entered guilty pleas in February 2025 to three felonies, including bail jumping, possession of methamphetamine and resisting/obstructing an officer.
The following month, Chelsea was given six years of probation, with two years awarded for each of the charges she pleaded guilty to. The conditions of her probation included remaining sober, not possessing alcohol or non-prescribed narcotics, not possessing firearms and not associating with people linked to drugs.
The comic served as a guest host for Jimmy Kimmel on his late night show last week while on summer vacation
Rosie shared a text message she had with Chelsea, talking about their goings-on
The mother and daughter pictured in New York in June 2016
Last October, Chelsea’s probation was revoked in connection with a 2025 incident, leading to the punishment.
Rosie, a mother of five, opened up in July Page six about getting back on the same page with her daughter after years of tension.
She said her prison visit to Chelsea earlier this summer was the “first conversation.” [she] in 10 years with her, that lasted more than 25 minutes.’
Rosie said that ‘the first time [she] I saw her consistently throughout the four hours in jail,” noting it was “the first time.” [she’d] I saw a kind of empathetic emotion from her.’
She called Chelsea “growing up” and added that she hopes “her future is brighter than the past decade.”
