The pupil response to speech masked by interfering speech was assessed across an intelligibility range from 0% to 99% correct. In total, 37 participants aged between 18 and 36 years and with normal hearing were included. Pupil dilation was largest at intermediate intelligibility levels, smaller at high intelligibility, and slightly smaller at very difficult levels. Participants who reported that they often gave up listening at low intelligibility levels had smaller pupil dilations in these conditions. Participants who were good at reading masked text had relatively large pupil dilation when intelligibility was low. We conclude that the pupil response is sensitive to processing load, and possibly reflects cognitive overload in difficult conditions. It seems affected by methodological aspects and individual abilities, but does not reflect subjective ratings.