Learners' monitoring judgments during reading are based on a variety of cues, and the roles of task features in promoting and constraining judgment accuracy are beginning to be understood. This work examined task and item characteristics influencing adults' monitoring of performance during reading and study tasks. In Study 1a, adults (N = 242) read an expository text, provided text ratings, completed comprehension items, and provided confidence judgments during testing. Readers' text complexity ratings predicted their item-level confidence, while their ratings of interest and cohesion predicted their bias scores. In Study 1b, the roles of linguistic features in predicting item-level monitoring estimates were examined using the comprehension items (item n = 23) from Study 1a. Selected item features, including length, ease, density, concreteness, and meaningfulness, were examined. Item ease significantly predicted item-level bias, while ease, density, concreteness, and meaningfulness predicted item-level confidence. Study 2 (N = 68) applied similar procedures to examine the effect of item feedback on the contributions of item features to learners' monitoring. Participants were randomly assigned to one of two item feedback conditions. Item density emerged as a significant predictor of item-level confidence, but only for those who first received item-by-item correctness feedback followed by massed feedback. Implications for future research are discussed.