Josh Duggar’s Raunchy Jail Messages to Anna Exposed

While awaiting sentencing on child pornography charges in 2022, Josh Duggar was busy writing love notes from jail — and they were anything but wholesome.

A series of explicit emails sent by the former 19 Kids and Counting star to his wife, Anna Duggar, while he was held at the Washington County Detention Center in Arkansas have been obtained by People — and they paint a picture of a man clearly untroubled by the fact that jail staff could read every word.

“[I] miss you my lover,” Josh, 38, wrote in one message sent in May 2022. “I miss being in the shower with you scrubbing, I miss watching you try on clothes, I miss watching you being sexy.”

In that same message, he congratulated Anna, 37, for “making the scale numbers lower than expected” and suggested she treat herself — specifically to “something low cut.” He then went further: “[O]r you can try on clothes and send me a pic of you in your bra and panties 😉 or try on ‘go to the private pool for sun’ swimsuit? btw you should order you a 2-piece swimsuit since summer is coming on soon, get something hot and fun.”

He closed the message with a wall of capital letters and emojis: “I LOVE YOU FOREVER! HUGS AND KISSES … AND EVERYTHING ELSE TOO! XOXOXOXOXO O: I LOVE YOU SEXY! x: :}v :}OvO.”

A few days later, when it seemed Anna hadn’t yet responded with photos, Josh followed up: “p.s. – send pics asap as requested, imlied [sic], inferred or otherwise stated lol. nice one(s) with your twos in it! (OvO).”

Anna apparently delivered. A week later, Josh confirmed he’d received at least one image and told her only one picture had come through — before asking what she was “thinking/dreaming/fantasizing about” and adding, “i cant wait till we can be alone again. i miss ALL of you!”

Just days before his sentencing, he was still at it. He told Anna he had “some great ideas of what we could be doing” — a list that started with “a really awesome foot rub” and “a back rub” before escalating. “And then we could really have some fun … once we were nice and relaxed! So many memories flooding my mind right now,” he wrote, also praising her: “your sexy cleavage is amazing! thank you for thinking of me!”

In another message around the same time, Josh described a new hobby he’d taken up behind bars — writing — framing it in intimate terms: “it was inverted, both of us going. both of us being alone. both of us enjoying our newest adventure. both of us having fun, with only us! both of us enjoying each other and taking things up a notch. the intensity is off the charts! You are gorgeous, sexy, and beautiful — all in one! you are my precious, lovely bride. my lover. my passion. my dream girl!”

The same month most of these messages were sent, Josh was sentenced to 151 months in federal prison after being convicted in December 2021 of receiving and possessing child sexual abuse materials. He and Anna, who married in September 2008, are parents to seven children: Mackynzie, Michael, Marcus, Meredith, Mason, Maryella, and Maydson.

He is currently serving his sentence at FCI Seagoville in Texas. His release date — originally set for August 2032 — has since been pushed back twice due to disciplinary violations, including possession of a contraband cell phone. It now stands at February 2, 2033. His cousin, Amy Duggar King, has claimed one of those violations landed him back in solitary confinement.

The Messages to Michelle: ‘You Don’t Get It’

The Anna emails aren’t the only correspondence making headlines. People also obtained messages Josh sent to his mother, Michelle Duggar, that reveal a very different side of his jail correspondence — angry, resentful, and pointed.

“[I] am very disappointed,” he wrote to Michelle. “I feel like you just don’t receive criticism or take admission for your own actions THAT HAVE DIRECTLY AFFECTED MY LIFE, including in this situation.”

He accused his parents of prioritizing their public image over their relationship with him, writing that “the public statements and pr work to save shows and public images i feel were placed above family relationships … and still are to this day.” He also reiterated his claim — which was rejected at trial — that another employee at his used car dealership had downloaded the illegal material found on his computer.

“I just think you don’t get it,” he wrote. “You don’t understand how you have hurt me and you keep trying to make yourselves ‘look good’ instead of trying to be concerned about your responses to my charges.”

In another message to Michelle, he complained that she had hung up on him during a phone call: “I was talking respectfully and I was trying to address something important. This is HURTING ME AND MY WIFE AND KIDS.” According to a psychologist who reviewed the emails, the pattern of Josh starting with gratitude before launching into criticism suggests someone “historically dismissed when they tried to communicate needs.”

He also wrote: “its hard to be here while everyone is out going and doing. its especially hard in light of how things have been since may 2015 when everything was devastated for Anna and I” — a reference to when the molestation allegations against him first became public. He said it felt like there were “18 kids and life went on.” Michelle, per People, largely did not acknowledge his criticisms, instead forwarding him messages of support from others.

The Family That Mostly Stayed Away

According to those same messages, only two of Josh’s 18 siblings reached out to him after his arrest. His brother John David Duggar — who had previously taken a hard public stance against Josh following the Ashley Madison cheating scandal — did video chat with him while he was detained locally, though he does not appear to have visited Josh at FCI Seagoville. His sister Jessa sent a note, but Josh said he’d heard nothing from any other siblings.

Jinger Vuolo made her position clear in a 2023 appearance on The Tamron Hall Show, saying she hadn’t spoken to Josh in years and had no plans to change that, adding she hadn’t seen any positive changes in him — though she said she continued to pray for his victims.

Jill Dillard, who is famously estranged from the broader Duggar family, has said she tried to send Josh mail but received no response, theorizing he refused her correspondence. She has made clear she has no interest in offering him forgiveness.

One brother who did make the trip to Seagoville: Joseph Duggar, who according to the U.S. Sun visited Josh in Texas in 2024. That visit carries its own uncomfortable context — Joseph was later arrested in March 2025 and charged with child molestation after a 14-year-old girl alleged he had touched her inappropriately multiple times during a family vacation when she was 9. He has pleaded not guilty and is demanding a jury trial. Josh, speaking through his attorney, called the allegations against Joseph “sensationalized fiction.”

Josh Duggar won’t be a free man until 2033 at the earliest. Anna, who stood by him through the molestation allegations, the Ashley Madison scandal, and now a federal prison sentence, is raising their seven children while he counts down the years — apparently one flirty email at a time.