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Description: Context drives our interpretations of music as surprising, satisfying, or scary. Despite a long-standing interest in musical prediction, it is unclear how listeners integrate context when performing a variety of tasks, and how this is influenced by expertise. We scrambled naturalistic music at multiple timescales to manipulate coherent context. Memory (E1; n=108, age 19-41) and prediction (E2; n=108, age 20-41) improved with more intact context for both musicians and non-musicians. Listeners’ event boundaries were influenced by the amount of tonal context but also reflected nested phrase structure, and musicians were more sensitive to longer-timescale “hyper-phrase” structure (E3; n=95, age 20-42) and could better identify the amount of scrambling (E4; n=108, age 19-41). These results indicate for the first time that listeners integrate context across complex phrases to efficiently encode, predict, and segment naturalistic music and that in general, training has surprisingly little impact on this integration.