Listening to speech in noise can be exhausting, especially for older adults with impaired hearing. Pupil dilation is thought to track the difficulty associated with listening to speech at various intelligibility levels for young and middle-aged adults. This study examined changes in the pupil response with acoustic and lexical manipulations of difficulty in older adults with hearing loss. Participants identified words at two signal-to-noise ratios (SNRs) among options that could include a similar-sounding lexical competitor. Growth Curve Analyses revealed that the pupil response was affected by an SNR × Lexical competition interaction, such that it was larger and more delayed and sustained in the harder SNR condition, particularly in the presence of lexical competition. Pupillometry detected these effects for correct trials and across reaction times, suggesting it provides additional evidence of task difficulty than behavioral measures alone.