We focused on the controversy whether high-performing readers consistently underestimate their comprehension or are prone to detrimental overestimations as much as less skilled readers are. Therefore, we conducted an experiment (N = 105 university students) to investigate judgment bias as a function of reading skill and text difficulty in terms of text cohesion. Results showed that the easy text produced underestimation of comprehension, whereas the hard text led to overestimation. Furthermore, readers with higher reading skills were less prone to overestimate their comprehension of a hard text than less skilled readers. However, we also found that more skilled readers showed lower sensitivity in discriminating between correct and incorrect answers than less skilled readers. Overall, our results do not support the idea that high-performing readers consistently underestimate their text comprehension. Findings are discussed with respect to readers’ awareness of different text-based judgment cues and their (beliefs about their) reading skill.