"Trouble with a Heartbreak" is a song written by Brett Beavers, John Morgan, Kurt Allison, and Tully Kennedy, and recorded by American country music artist Jason Aldean.

Billy Dukes of Taste of Country wrote that the song "recalls slower songs" from Aldean's "My Kinda Party and Night Train era, but there's a drop of R&B production that makes one think of They Don't Know, his most progressive album to date," while also hinting it recalls "heartbreak as something of a bruise that is very slow to heal; everyone has advice on how to "move on," but none of it is any good.

"[4] An uncredited review from Off the Record UK called it "a haunting track that showcases a more vulnerable side to Aldean’s musicality.

"[5] Upon its release, "Trouble with a Heartbreak" was added to the playlists of 84 country music radio stations surveyed by Mediabase, making it the most-added new song for the week of January 18, 2022.

Directed in December 2021 by Shaun Silva, the video features concert footage from Aldean's three-day concert at the Park Theater in Las Vegas, Nevada, interspersed with footage of a cowboy at the National Finals Rodeo in the same city.