Inside Jill Duggar's Relationship With Sister-In-Law Anna Duggar

After Josh Duggar was found guilty of receiving and possessing child sexual abuse material, his sister Jill Duggar and her husband, Derick Dillard, shared their thoughts about a federal judge's decision to sentence Josh to over 12 years in prison. "It is unfortunate, but it seems that it may take spending over a decade in federal prison, and still more on probation, for Josh to have any potential for rehabilitation to the point he can safely live in society again," the couple wrote on their website.

Josh's trial and subsequent imprisonment created some complicated family dynamics. Not everyone seemed to agree with Jill and Derick's acceptance of Josh's fate, as evidenced by a letter that Anna Duggar penned on her husband's behalf. Her aim was to convince the judge to hand Josh a more lenient sentence, and it was clear that she was standing by her man. "I ask that you consider reuniting us as a family again soon," Anna wrote in part, per KNWA's Fox 24.

Anna spent a lot of time around her in-laws while filming the reality series "19 Kids and Counting," and the Duggar family rallied around her in 2015 after Josh released a statement on his family's website confessing that he had been unfaithful. Months earlier, Jill had appeared on "The Kelly File" to say that she'd forgiven her brother for molesting her when he was a teenager. Jill has hinted that she still supports Anna despite their disagreement about Josh's prison sentence.

How Anna Duggar helped one of Jill Duggar's sons

Jill Duggar and Derick Dillard aren't holding Anna Duggar's unwavering support for her husband against her. "We continue to love Josh and his family and will be there for them however we can," the couple wrote on their website. According to People, Dillard was spotted sitting beside Anna and chatting with her during Josh's trial in December 2021, and a few weeks later, Jill provided further proof that she and her sister-in-law were still on good terms when she mentioned Anna on Instagram.

In response to a follower's question about her son Sam's reading level, Jill wrote, "My SIL @annaduggar got us hooked on @preschoolprepcompany videos (several can be found on YouTube Kids) to help learn phonics blends, sight words, etc. It has helped both our boys SO much!!"

Anna is a stay-at-home mother of seven, so she'll likely require plenty of help herself while her husband serves his prison sentence. Josh and Jill's cousin Amy Duggar told The Sun that she offered to let Anna and the kids stay with her, but Anna wasn't responding to her efforts to reach out. A family insider offered some insight into why Anna might also spurn other family members, including Jill. "Anna is still speaking to [Jim Bob Duggar] and [Michelle Duggar], but a lot of the siblings have distanced themselves," the source told In Touch. "She was upset that some family members decided to speak out against Josh. That broke her heart."

Jill and Anna had different feelings about Counting On

Jill Duggar and Anna Duggar interacted regularly on "19 Kids and Counting." Jill even got some hands-on midwife training by helping Anna out when the birth of her third child, Marcus, was captured on camera in 2013, per the Duggar Family Blog. But after In Touch broke its story about Josh molesting his sisters, TLC quit filming him and renamed the series "Counting On." Anna, however, continued making occasional appearances with her in-laws. In the show's second episode, Jill described how she reacted to Josh's infidelity admission. "I said, 'I need to call Anna, because I can't imagine what she feels right now,'" she recalled, per Us Weekly.

In 2017, Jill and Derick Dillard quit appearing on "Counting On." They later told People that they had grown frustrated because the show was causing them to miss out on other opportunities, and in court documents obtained by E! News, Jill singled out her dad, Jim Bob Duggar, as one of their main sources of conflict. "Sadly, I realized he had become pretty controlling, fearful and reactionary," Jill said.

Meanwhile, Anna strongly hinted that she wanted to spend more time filming with her father-in-law and the rest of the family. "It means a lot when our family is included (on rare occasions) in the events that air on tv with Joshua's family," she wrote in an August 2020 Instagram post. Less than a year later, TLC canceled "Counting On."