On January 15, 2019, Struggle and his oldest daughter, singer Brianna Harness, released a collaborative EP entitled Sunny Days which snagged the #3 spot on Billboard Blues Albums charts.
The LP titled The Widow's Son included guest appearances by Bubba Sparxxx, Jeremy Penick, Julie Roberts, Alexander King and Yelawolf.
On November 15, 2019, Jennings released the full-length album entitled Angels & Outlaws featuring 11 tracks in collaboration with his guitarist Trap DeVille and his daughter and music newcomer, Brianna Harness.
In June 2020, Jennings teamed up with Adam Calhoun for the EP "Legends" and in December 2020, fans were surprised by the long anticipated release of "Waylon & Willie IV", the fourth record in the collaboration series between Struggle and his fellow Nashville native, Jelly Roll.
In 2021, Jennings can be found touring and working with artists Brianna Harness and Caitlynne Curtis to advance their independent careers via his label "Angels & Outlaws" based in Nashville.