AbstractEffort during listening is commonly measured using the task‐evoked pupil response (TEPR); a pupillometric marker of physiological arousal. However, studies to date report no association between TEPR and perceived effort. One possible reason for this is the way in which self‐report effort measures are typically administered, namely as a single data point collected at the end of a testing session. Another possible reason is that TEPR might relate more closely to the experience of tiredness from listening than to effort per se. To examine these possibilities, we conducted two preregistered experiments that recorded subjective ratings of effort and tiredness from listening at multiple time points and examined their covariance with TEPR over the course of listening tasks varying in levels of acoustic and attentional demand. In both experiments, we showed a within‐subject association between TEPR and tiredness from listening, but no association between TEPR and effort. The data also suggest that the effect of task difficulty on the experience of tiredness from listening may go undetected using the traditional approach of collecting a single data point at the end of a listening block. Finally, this study demonstrates the utility of a novel correlation analysis technique (“rmcorr”), which can be used to overcome statistical power constraints commonly found in the literature. Teasing apart the subjective and physiological mechanisms that underpin effortful listening is a crucial step toward addressing these difficulties in older and/or hearing‐impaired individuals.