At the time, Eugenie was 19 — just days shy of her 20th birthday — and Epstein had already been convicted of a sex crime involving a minor

Sarah Ferguson made a vulgar remark about her then-19-year-old daughter to Jeffrey Epstein in an email that has come to light through the latest round of Epstein-related files released by the U.S. Department of Justice (DOJ).

On Friday, Jan. 30, the DOJ unsealed over 3 million files from the criminal investigations into the late financier and convicted sex offender. In one of the emails, the former Duchess of York, 66, seemingly responded to an inquiry from Epstein with a crude comment about Princess Eugenie, the youngest of her two daughters with ex-husband Andrew Mountbatten-Windsor, the former Prince Andrew.

In one email reviewed by PEOPLE from March 2010, Esptein asks Ferguson about taking a trip to New York. In response, she replied, “Not sure yet. Just waiting for Eugenie to come back from a shagging weekend!!”

At the time, Eugenie, now 35, was 19 years old and just two days shy of her 20th birthday. She was spending time with her then-boyfriend, Jack Brooksbank, to mark the occasion, per The Mirror.

The email exchange also came after Epstein had already been convicted and jailed for a sex crime involving a minor.

Sarah Ferguson with daughters Princess Beatrice (left) and Princess Eugenie (right). Dave Benett/Getty

In June 2008, Epstein pleaded guilty to charges of solicitation of prostitution and solicitation of prostitution with a minor under the age of 18. He was sentenced to serve 18 months in a minimum-security prison, and he was later released from the facility in 2009. He then began serving a house arrest sentence, which ended in August 2010.

A spokesperson for Ferguson declined to comment when reached by PEOPLE. Buckingham Palace did not immediately respond to PEOPLE’s request for comment.

Ferguson also shares daughter Princess Beatrice, 37, with Andrew, 65, who was stripped of his royal titles last fall amid reignited scrutiny over his own relationship with Epstein.

In another email sent in 2010, Ferguson reportedly told the late sex offender to “just marry me.”

“You are a legend. I really don’t have the words to describe, my love, gratitude for your generosity and kindness. Xx I am at your service. Just marry me,” Ferguson wrote in the message that January, according to the Daily Mail.

Ferguson had also told Epstein to “marry” her in a previous email dated September 2009, according to the outlet.

Andrew also appeared in email exchanges and photos released in the latest batch of Epstein files, including pictures of the former royal kneeling on all fours over an unidentified woman on the ground.

The DOJ’s December release of files featured a photo of Andrew sitting with Epstein co-conspirator Ghislaine Maxwell inside the saloon at Sandringham House, one of the late Queen Elizabeth’s most beloved royal estates.

Maxwell, 64, is currently serving a 20-year prison sentence after she was convicted of sex trafficking in 2021. Andrew, meanwhile, has repeatedly denied any wrongdoing in relation to his ties to Epstein.

Andrew stepped back from his public royal role in 2019 following a headline-making BBC interview, in which he discussed his relationship with Epstein. The former royal has been connected to Virginia Giuffre, an outspoken Epstein victim who has alleged that she was made to have sex with Andrew when she was just 17 years old. (Giuffre died by suicide at age 44 in 2025.)

Prime Minister Sir Keir Starmer has since suggested that Andrew testify before Congress in the United States in relation to his ties to Epstein.

“In terms of testifying, I have always said anybody who has got information should be prepared to share that information,” Starmer, 63, told reporters, per the BBC. “You can’t be victim-centred if you’re not prepared to do that. Epstein’s victims have to be the first priority.”

Jeffrey Epstein.Rick Friedman/Rick Friedman Photography/Corbis via Getty

Can’t get enough of PEOPLE’s Royals coverage? Sign up for our free Royals newsletter to get the latest updates on Kate Middleton, Meghan Markle and more!

The release of the emails detailing correspondence between Ferguson and Epstein comes as the deadline for the former Duchess of York to vacate Royal Lodge, the Windsor Great Park residence she has shared with Andrew, approaches.

As of Jan. 30, she was still searching for her next home and will be overseas for the next few weeks while weighing her options, PEOPLE understands.

After Ferguson and Andrew welcomed their two daughters, they separated in 1992 and divorced in 1996, but they remained close and continued to live together at Royal Lodge.

Over the years, both have made headlines for their respective relationships with Epstein, who died in an apparent suicide while awaiting trial one month after he was arrested and charged with sex trafficking of minors in July 2019.

Not long after Ferguson’s newly released 2010 email exchanges with Epstein, news that the late financier was involved in helping to pay off debts she owed to staff members became public, and she issued a public apology in a March 2011 interview with the Evening Standard.

At the time, she expressed deep regret over her decision to accept the convicted sex offender’s help, calling it a “terrible, terrible error of judgment.” She also said, “I abhor paedophilia.”

The following month, however, Ferguson was reported to have written privately to Epstein, apologizing for comments she said were made to protect her career and referring to him as a “steadfast, generous and supreme friend,” per a leaked email published by The Sun years later.

If you or someone you know has been a victim of sexual abuse, text “STRENGTH” to the Crisis Text Line at 741-741 to be connected to a certified crisis counselor.

This Hidden Policy Is A Game Changer For Costco Members