Recorded live at Nashville's Oceanway Studios, Crooked Tree was produced by Tuttle and Jerry Douglas and features collaborations with Sierra Hall, Old Crow Medicine Show, Margo Price, Billy Strings, Dan Tyminski, and Gillian Welch. The album explores Tuttle's lifelong love of bluegrass-a genre she first discovered though her father, a music teacher and multi-instrumentalist, and her grandfather, a banjo player. Across these thirteen original tracks, all written or co-written by Tuttle, she simultaneously honors the bluegrass tradition while also pushing the genre in new directions. Tuttle says, "I always knew I wanted to make a bluegrass record someday. Once I started writing, everything flowed so easily: sometimesI've felt an internal pressure to come up with a sound no one's heard before, but this time my intention was just to make an album that reflected the music that's been passed down through generations in my family. I found a way to do that while writing songs that feel true to who I am, and it really helped me to grow as a songwriter."