After Chicken Truck broke up, Henneman played occasional shows as a solo acoustic act, and sometime in late 1990 he began working as a roadie for Uncle Tupelo, occasionally playing extra guitar or mandolin with them. He became a staple during their encores, and played lead guitar on "Cortez the Killer", "Moonshiner", and many other covers. He also played extensively on the albums "Still Feel Gone" and "March 16–20, 1992", and also on some of the Uncle Tupelo tracks that ended up on various compilations ("Blue Eyes" and "Movin' On").