Listening to speech in noise can require substantial mental effort, even among younger normal-hearing adults. The task-evoked pupil response (TEPR) has been shown to track the increased effort exerted to recognize words or sentences in increasing noise. However, few studies have examined the trajectory of listening effort across longer, more natural, stretches of speech, or the extent to which expectations about upcoming listening difficulty modulate the TEPR. Seventeen younger normal-hearing adults listened to 60-s-long audiobook passages, repeated three times in a row, at two different signal-to-noise ratios (SNRs) while pupil size was recorded. There was a significant interaction between SNR, repetition, and baseline pupil size on sustained listening effort. At lower baseline pupil sizes, potentially reflecting lower attention mobilization, TEPRs were more sustained in the harder SNR condition, particularly when attention mobilization remained low by the third presentation. At intermediate baseline pupil sizes, differences between conditions were largely absent, suggesting these listeners had optimally mobilized their attention for both SNRs. Lastly, at higher baseline pupil sizes, potentially reflecting overmobilization of attention, the effect of SNR was initially reversed for the second and third presentations: participants initially appeared to disengage in the harder SNR condition, resulting in reduced TEPRs that recovered in the second half of the story. Together, these findings suggest that the unfolding of listening effort over time depends critically on the extent to which individuals have successfully mobilized their attention in anticipation of difficult listening conditions.