Songfacts®:

• This bluesy, rootsy song finds Chris Stapleton talking to his former partner in a messy relationship. They have met up for a reunion and Stapleton realizes the attraction is still there. He tells the girl she should step away before they give in to temptation and do something they will later regret.
  
  'Cause I know you and you know me
  And we both know where this is gonna lead
  You want me to say that I want you to stay
  So you should probably leave
• There is a twist in the third verse when Stapleton reveals they spent the night together. It is now the next morning, and the singer hopes when his ex-wakes up, she doesn't think it was a mistake and tell him he should leave.
• Chris Stapleton wrote the song with two fellow Nashville songwriters: Chris DuBois and Ashley Gorley. It is the oldest track on Starting Over with various performances of it from the mid-2010s uploaded to YouTube, including one from Musicians Corner in Nashville in October 2014.
• Stapleton originally recorded "You Should Probably Leave" for a previous album. The record got canned after its lead single, "What Are You Listening To," did not perform as expected.
  
  It was actually Stapleton's wife and backing singer Morgane that persuaded him to include the song on Starting Over. She told him it was time for "You Should Probably Leave" to be officially released into the world, having garnered a following on YouTube.
• "You Should Probably Leave" climbed to #1 on the Country chart dated February 15, 2022. It was Stapleton's third visit to the tally's summit, following "Tennessee Whiskey" and "Starting Over."
• This won for Best Country Solo Performance at the Grammy Awards in 2022. "Cold," which Stapleton performed at the ceremony, won Best Country Song, and Starting Over earned Best Country Album.