As a young child, Kendra lived in Woodbridge, Virginia, where her father was a pastor at Heritage Baptist Church. In 2008, her father was sent by Baptist International Missions, Inc. to plant a church in Fayetteville, Arkansas. Kendra lived with her family there until she got married.
Kendra was homeschooled alongside her siblings.
She met her future husband Joseph Duggar while attending Lighthouse Baptist Church, where her father is the pastor. On March 7, 2017, Joseph Duggar asked Kendra to court him in the lot where his childhood home once was. He presented her with a promise ring, which the other Duggars have never done. They announced their courtship with a TLCGo video released online.
Joseph proposed on May 26, 2017 at his sister Joy-Anna's wedding reception. Joy pretended to toss the bouquet into the crowd of eligible women, but turned and handed it to Kendra instead. Joseph then came up to her and proposed. This proposal is featured in the Counting On episode "Joy's Wedding".
Kendra married Joseph Duggar on September 8, 2017, at First Baptist Church in Siloam Springs, Arkansas. Her sister Lauren was her maid of honor, and she had ten bridesmaids including her mother Christina Caldwell and future sisters-in-law Jana, Johannah, Jennifer, Jill, Jessa, Jinger, and Joy-Anna. Her sister Olivia Caldwell was her flower girl, and her brothers Nathan and Timothy were the ring bearers.
For their honeymoon, the couple visited Athens, Greece.
On December 18, 2017, Kendra and Joseph announced that they are expecting their first child. On June 8, 2018, Kendra gave birth to her first child, a son named Garrett David. He weighed 7 lbs, 8 oz, and was 20 ½ inches long.
On April 11, 2019, they announced that they are expecting their second child. On June 25, 2019, they revealed that they are having a girl. Their daughter, Addison Renee was born on November 2, 2019 at 5:33 am. weighing 7 lbs 12.5 oz and measuring 20 ½ inches.
On August 19, 2020, they announced that they are expecting their third child, due in February 2021. On November 30, 2020, they revealed that they are having another girl. Their second daughter, Brooklyn Praise was born on February 19, 2021, at 7:48 pm., weighing 7 lbs, 3 oz and measuring 20.25 inches.