At the beginning of 1968, Van Morrison became embroiled in a contract dispute with Bang Records following the sudden death of the label's founder, Bert Berns, from a heart attack on December 30, 1967. Prior to Berns's death, he and Morrison had experienced creative conflicts, as Berns pushed for a more pop-oriented sound while Morrison sought to explore new musical directions. Ilene Berns, Bert's widow, blamed Morrison for her husband's death but later downplayed this view. Morrison's then-girlfriend, Janet Rigsbee, described Ilene's subsequent vindictiveness toward him.

After Bert Berns's death, Ilene Berns inherited the contracts of Bang Records. Morrison's annual option on his recording contract was due shortly after the funeral. Bound to Bang Records, he was unable to record or secure performances in New York, as many clubs avoided booking him out of fear of reprisals due to Berns's connections to organized crime. Ilene Berns also attempted to have Morrison deported due to his lack of proper immigration paperwork. He managed to stay in the U.S. when Rigsbee agreed to marry him. After their marriage, they moved to Cambridge, Massachusetts, where he began performing in local clubs. Morrison started with a small electric combo, playing blues and songs from Blowin' Your Mind! and his time with Them. When two musicians left, he retained bassist Tom Kielbania from the Berklee School of Music. Morrison then shifted to an acoustic sound, performing as a duo with Kielbania in Boston coffeehouses, which allowed for greater vocal improvisation and a freer, folkier feel.