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If language users are rational, they might choose to structure their utterances so as to optimize communicative properties. In particular, information-theoretic and psycholinguistic considerations suggest that this may include maximizing the uniformity of information density in an utterance. We investigate this possibility in the context of syntactic reduction, where the speaker has the option of either marking a higher-order unit (a phrase) with an extra word, or leaving it unmarked. We demonstrate that speakers are more likely to reduce less information-dense phrases. In a second step, we combine a stochastic model of structured utterance production with a logistic-regression model of syntactic reduction to study which types of cues speakers employ when estimating the predictability of upcoming elements. We demonstrate that the trend toward predictability-sensitive syntactic reduction (Jaeger, 2006) is robust in the face of a wide variety of control variables, and present evidence that speakers use both surface and structural cues for predictability estimation.