Rosie O’Donnell took to Instagram Thursday with a picture of her as she posed with her daughter Chelsea, who is currently serving a prison sentence, while sharing a text message exchange they had.
The 64-year-old comic, who served last week as a guest host for Jimmy Kimmel on his late night show during his summer break, kept up-to-date in her text exchange with Chelsea, 28.
In an accompanying photo, which appeared to be snapped in June when O’Donnell visited Chelsea in prison, Rosie wore a black shirt while Chelsea was clad in a button-up green top, with both smiling.
In the text exchange, Chelsea said to her mother, ‘Thank you mom I got my music back today.
‘How are you? I’m trying to get ahold of the social worker to let her know the plans for when i get out, Hannah texted her for me.’
Rosie replied, ‘Ok great – got my nails done – no more gel for me my nails are ruined,’ prior to asking her, ‘Are u reading a good book?’
Rosie O’Donnell, 64, took to Instagram Thursday with a picture of her as she posed with her daughter Chelsea, 28, who is currently serving a prison sentence, while sharing a text message exchange they had
Chelsea replied, ‘I am reading the legacy series … its really good she has a bunch of other books too.
‘And yeah I [haven’t] painted my nails in years but I remember that stuff breaking my nails.’
The Daily Mail has reached out to representatives for O’Donnell for further comment on the story.
Chelsea is in the midst of an 18-month prison sentence she is serving at Taycheedah Correctional Institution in Fond du Lac, Wisconsin.
She had been sentenced in October of 2025 after multiple violations of her probation linked to guilty pleas from a series of 2024 arrests.
In her 2024 arrests, Chelsea had been taken into custody in connection with felony charges including methamphetamine possession and child neglect.
Chelsea in February of 2025 entered guilty pleas to three felonies, including bail jumping, methamphetamine possession and resisting/obstructing an officer.
The following month, Chelsea received six years of probation, allotting two years for each of the charges she pleaded guilty to. Among the terms of her probation included staying sober, not possessing any alcohol or non-prescribed narcotics, not possessing any firearms and not associating with people linked to drugs.
The comic served last week as a guest host for Jimmy Kimmel on his late night show during his summer break
Rosie shared a text message exchange she had with Chelsea speaking about their ongoings
The mother and daughter pictured in NYC in June of 2016
Last October, Chelsea’s probation was revoked in connection with a 2025 incident, leading to the sentence.
Rosie, who is mother to five children, in July opened up to Page Six about getting back on the same page with her daughter following years of tension.
She said that her prison visit to Chelsea earlier this summer marked the ‘first conversation [she] had with her in 10 years that lasted more than 25 minutes.’
Rosie said that ‘the first time that [she] saw her in a consistent way was the four hours in the prison,’ noting that it marked ‘the first time [she’d] seen, kind of, an empathetic emotion from her.’
She credited Chelsea for ‘growing up,’ adding that she hopes ‘her future is brighter than this past decade has been.’
