Anna Duggar advises Joseph on jail life, sends money to help him contact wife Kendra

Anna emailed Joseph days after his arrest, offering practical tips about jail routines and helping him stay connected with his wife while in custody
PUBLISHED APR 3, 2026
Joseph Duggar depended on sister-in-law Anna Duggar for guidance and support while he was in custody (Little Duggar Family/Instagram, @duggarfam/Instagram)
Joseph Duggar depended on sister-in-law Anna Duggar for guidance and support while he was in custody (Little Duggar Family/Instagram, @duggarfam/Instagram)

TONTITOWN, ARKANSAS:  At a county detention facility, Joseph Duggar relied on two women for support. One was his wife Kendra Duggar. The other was Anna Duggar, the wife of his older brother Joshua.

Anna sent Joseph a long email to support him. She said the family loves him and is there for him. She also told him to let them know if he needed any help. She added that she had put money into his account. This would help him buy things from the commissary and pay for phone calls to Kendra.

The email was sent on March 21, three days after he was taken into custody. They later exchanged several emails. Anna also shared tips on how to deal with time in solitary confinement. Her husband is currently serving a 12-year federal prison sentence in Texas.

Anna Duggar and Josh Duggar pose during the 42nd annual Conservative Political Action Conference (CPAC) at the Gaylord National Resort Hotel and Convention Center on February 28, 2015 in National Harbor, Maryland. Conservative activists attended the annual political conference to discuss their agenda. (Photo by Kris Connor/Getty Images)
Anna Duggar and Josh Duggar posed during the Conservative Political Action Conference in Maryland in February 2015 (Kris Connor/Getty Images)

Anna Duggar shares advice with Joseph Duggar about life in jail

Anna Duggar’s long email to Joseph Duggar was revealed. In it, she tried to help him understand life in jail. She also offered to help set up calls if he needed it.

"Just remember, don’t talk about anything legal unless you are with an attorney. Everything said in these messages, phone calls, and video chats are recorded and turned over to prosecutors," Anna writes to Joseph in the email.

She also said that "Joshua’s experience there at Washington County was fairly safe," and told Joseph to contact her "if there are any concerns for your health, or safety." Anna explained that the "commissary has a two-week delay," and told him to check if that was still true.

Accused Joseph Duggar attended a virtual hearing in Arkansas in the wake of his Wednesday, March 18 arrest (Washington County Sheriff's Department)
Joseph Duggar attended a virtual hearing following his arrest on March 18 (Washington County Sheriff's Department)

She added that "if you will be there a while, we definitely want to send some goodies your way." At the end of the email, she spoke about Kendra and signed off by writing, "Praying for ya, love ya. Anna."

They later exchanged eight emails. Joseph could not reach Kendra that morning, so he asked Anna for help. She helped him get in touch with his wife. She also gave him another tip, saying, "You can put in a request to the chaplain to visit you; he can give you more books too," Anna told Joseph.

Joseph Duggar held at Bay County Jail after lewd behavior charges

Kendra Duggar once described her marriage to Joseph as joyful before his arrest (@littleduggarfamily/Instagram)
Kendra Duggar previously spoke about her marriage to Joseph Duggar before his arrest (@littleduggarfamily/Instagram)

Joseph is currently out on a $600,000 bond after appearing before a Florida judge on Tuesday, March 31. He had been held at Bay County Jail after the Bay County Sheriff’s Office charged him with two counts of lewd and lascivious behavior on March 18.

The case is linked to claims that he acted inappropriately toward a 9-year-old during a 2020 family trip to Panama City Beach. Joseph has filed a written plea of not guilty to the charges.

As part of his pretrial release, he is not allowed to have any unsupervised contact with anyone under the age of 18, including his four children.

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