The ability to generalize across specific experiences is vital for the recognition of new patterns, especially in speech perception considering acoustic–phonetic pattern variability. Indeed, behavioral research has demonstrated that listeners are able via a process of generalized learning to leverage their experiences of past words said by difficult-to-understand talker to improve their understanding for new words said by that talker. Here, we examine differences in neural responses to generalized versus rote learning in auditory cortical processing by training listeners to understand a novel synthetic talker. Using a pretest–posttest design with EEG, participants were trained using either (1) a large inventory of words where no words were repeated across the experiment (generalized learning) or (2) a small inventory of words where words were repeated (rote learning). Analysis of long-latency auditory evoked potentials at pretest and posttest revealed that rote and generalized learning both produced rapid changes in auditory processing, yet the nature of these changes differed. Generalized learning was marked by an amplitude reduction in the N1–P2 complex and by the presence of a late negativity wave in the auditory evoked potential following training; rote learning was marked only by temporally later scalp topography differences. The early N1–P2 change, found only for generalized learning, is consistent with an active processing account of speech perception, which proposes that the ability to rapidly adjust to the specific vocal characteristics of a new talker (for which rote learning is rare) relies on attentional mechanisms to selectively modify early auditory processing sensitivity.