A challenge for listeners is to learn the appropriate mapping between acoustics and phonetic categories for an individual talker. Lexically guided perceptual learning (LGPL) studies have shown that listeners can leverage lexical knowledge to guide this process. For instance, listeners learn to interpret ambiguous /s/-/∫/ blends as /s/ if they have previously encountered them in /s/-biased contexts like epi?ode. Here, we examined whether the degree of preceding lexical support might modulate the extent of perceptual learning. In Experiment 1, we first demonstrated that perceptual learning could be obtained in a modified LGPL paradigm where listeners were first biased to interpret ambiguous tokens as one phoneme (e.g., /s/) and then later as another (e.g., /∫/). In subsequent experiments, we tested whether the extent of learning differed depending on whether targets encountered predictive contexts or neutral contexts prior to the auditory target (e.g., epi?ode). Experiment 2 used auditory sentence contexts (e.g., *I love “The Walking Dead” and eagerly await every new…*), while Experiment 3 used written sentence contexts. In Experiment 4, participants did not receive sentence contexts but rather saw the written form of the target word (episode) or filler text (########) prior to hearing the critical auditory token. While we consistently observed effects of context on in-the-moment processing of critical words, the size of the learning effect was not modulated by the type of context. We hypothesize that boosting lexical support through preceding context may not strongly influence perceptual learning when ambiguous speech sounds can be identified solely from lexical information.